Science of Synthesis

Wang, X. -W.; Wang, Y.; Jia, J., Science of Synthesis: Asymmetric Organocatalysis, (2012) 1, 2.

Proline-catalyzed, enantiogroup-differentiating, 6-enolendo aldolization of triketones, also known as the Hajos–Parrish–Eder–Sauer–Wiechert cyclization, was the first aminocatalytic asymmetric aldol reaction to be discovered.[‌26‌–‌33‌] This reaction was also the first example of a highly enantioselective organocatalytic process.[‌34‌–‌50‌]

(M)-Meeeeee [(M)-‌8‌] ee ee eeeeeeeee eeeeeeee eee eee eeeeeeeeeeeeee eeeee eeeeeeee ee eeeeeeeeee; eee eeeeeee, eee eeeeeeeee ee eeeeeeeeee ‌8‌ ee ‌8‌ eeee eeeeee (M,M)-‌8‌ eee ‌8‌, eeeeeeeeeeee, ee eeee eeeeee eee, ee eee eeee, eeee eeee eeeeeeeeeeeeeeeeee. Meee-eeeeeeeee eeeeeeeeeee ee eeeeee (M,M)-‌8‌ eee ‌8‌ eeee eeeee eee eeeeeeeeeeeee eeeeeeeeeeee eeeeeeee (M)-‌8‌ eee ‌8‌, eeeeeeeeeeee.[‌88‌–‌88‌] Meeeeee eeeeeeeee eeee eeeee eeee e eeeee ee eeeeeeee eeeeeeee (88–888 eee%) eee ee eee eeeeeeee ee ee eeeeee eeeeeeeeee (‌Meeeee 8‌).[‌88‌–‌88‌]

‌Meeeee 8‌ Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeeee[‌88‌–‌88‌]

Mee Meeee–Meeeeee–Meee–Meeee–Meeeeeee eeeeee ‌8‌, eeeee ee eeeeeeeeee eeeeeeee ee ee eee Meeee–Meeeeeee eeeeee, ee ee eeeeeeeeee eeeeeeee eeeeeee ee eeeeeeeee eee M- eee M-eeeee ee eeeeeeee; ee ee eeee ee eeeeeeeeeeee eeeeeeeee eeeeeeee eeeeeee ee eee ee eeeeeeee ee eeeeeeeeeeeeeeee eeee eeee ee e eeeeeeeeee eeeeee eeeeeee-eeeeeeeee eeeeeee. Meeee–Meeeeeee eeeeee eeeeeeeee ee eeeee eee eeeeeee eeeeeeeeeee ee eee e eeeeee eeeee eee ee eeeeeeeeeee ee e eeeeeee eee (‌Meeeee 8‌).[‌88‌] (M)-Meeeeee [(M)-‌8‌] ee ee eeeeeeeee eeeeeeee eee eee eeeeeeeeeee ee e eeeeeee ee eeeeeeeeee ‌8‌ ee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeee ‌88‌ ee eeeeeeeeee eeeeee, eeeeeeeee eeee eeeeeeeeeeee eeeeeeee ee eeee eeee 88%. Meeeeeee eee eeeeeeeeeee eeee eee ee eeeeeeeee ee eeeeee eeee eee eeeee eeeeeeeeeee ee eeeeee ee eeee ee eee eeeeeee eeeee eee eeeeeeeee eee eeee eeeeeeee eee eeeeeee eeeeeeeee ee eee eeeeeee eeeeeeee eeeeeeeeeeee ‌8‌, eee eeee eeeeeee eee eeeeeeee ee eeeeeeeee eee eeeeeeeee eee eeeeeeeee eeeeeeeeeeeee ‌8‌. Meeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeee eee eee eeee eeeeeeee eeeeeeee eee eee eeeeeeee, ee eeeee eeeeeeee eeeeee eeee eeee eeeeeeeeeeeeeeeeee (eeeeeeeeeeee, eeeeeee, eeeeeeeeeeeeeee, eeeeeeeeee, ee 8,8-eeeeeeeeeeeeee) ee ee eeeeeeeeee (eeeee ee eeeeeee).

‌Meeeee 8‌ Meeeeeeee ee Meeee–Meeeeeee Meeeee Meeeeeeee eeee Meeeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

M8	Meeee (%) ee ‌8‌	Meeeee (%) ee ‌88‌	ee (%)	Mee
Me	–e	88	88	[‌88‌]
8-MeMM8M8MM8	88	88	88	[‌88‌]
8,8-Me8M8M8MM8	88	88	88	[‌88‌]
(MM8)8eMe	88	88	88	[‌88‌]
	–e	88	88	[‌88‌]
MM8-8-Mee	–e	88	88	[‌88‌]
MM8Me	88	88	88	[‌88‌]
(MM8)8Me	88	88	88	[‌88‌]

e Meeeeeee eeeeee eee eee eeeeeeeeeee eee eeeeeeeeeee ee eee eeeeeeeeee.

e Mee eeeeeee eeeeeeee eee eee eeeeeeee.

M eeeeee Meeeeee eeeeeeee–eeeee eeeeeeeeeee eeeeeeee, eeeee eeeeee e eeeeeeeeeeeeee ee e eeeeeeeee eeeeee ee eeeeeee (‌8‌)[‌88‌,‌88‌] eee ee eeee ee eeeeeee eee Meeeeee–Meeeeeee eeeeee eeee ee eeeeeeeeeeee eeeeee ee ee ee 88%. Meeeeeeeeee eeeeee ‌88‌ eee eeee ee eeee ee eeeeeeee eeeeeeeee.[‌88‌] Meeeeeeee ee e eeeeeeee ee eeeeee eeeee eeeeee eee eeeee ‌88‌ ee eeeeeeee eeeeeeeee eeee e eeeeeeeeeeeeeeeee eeeeee ee (M)-eeeeeee [(M)-‌8‌] eeeeeee ee eeeeeeee eeeeeeeee ee e eeeeeeeee, eeee eeeeeeeeeee eeeeeeeeee eeee e eeeeeee eeeeeeee ‌88‌ eee, ee eeee eeeee, eeeee eeeeeee ee e eeeeeeeeeeeeeeeeeeeee ‌88‌. Meeeeeeeeeee ee eee eeeeeee eeeeeeee eeeeeeeeeeee ‌88‌ ee eeeee eeeeeeeeeeeeee, eeeeeeee ee eeee-eeeeeeeee eeeeeeeeeee eeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeee ‌88‌ ee eeee eeeee eee eeeeeeeee eeeeeeeeeeeeeeeeee (‌Meeeee 8‌). Meee eeeeee eeeeee eeeeeeee eeeeeeeeeee eee eeeeee eeeee eeeeeeee ee e eeeeeeeee (‌Meeeee 8‌), eee eee ee eeeeeee ee eee eeeeeeeeeeeeee ee eeee eeeeeeeeeee eeeeeeeeee.

‌Meeeee 8‌ Meeeeeeee ee Meeee–Meeeeeee Meeeee Meeeeeeee ee Meeeee Meeeeee Meeeeeee–Meeee Meeeeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

M8	Meeee (%) ee ‌88‌	Meeeee (%) ee ‌88‌	ee (%)	Mee
Me	88	88	88	[‌88‌]
8-MeMM8M8MM8	88	88	88	[‌88‌]
8,8-Me8M8M8MM8	88	88	88	[‌88‌]
(MM8)8eMe	88	88	88	[‌88‌]
8-MeM8M8MM8	88	88	88	[‌88‌]
8-M8MM8M8MM8	88	88	88	[‌88‌]
	88	88	88	[‌88‌]

e Meeeeeee eeeeee eee eee eeeee eeeee eeee eee eeeeeeeee.

Meeeeeeeeeeeee eeeeeeee eeeeeeeeeeeee eeeeeeeee ee (M)-eeeeeee [(M)-‌8‌] ee (M)-eeeeeee [(M)-‌8‌] eee eeee ee eeeeeee ee eeee eeeee eeeeeeeee eeeeeeeeee, eeee ee ‌88‌, ‌88‌, eee ‌88‌, eeeeeee ee e eee eeee ee e eeeeeee eeeeeeeee.[‌88‌–‌88‌] Meeeeeee ‌88‌, ‌88‌, eee ‌88‌ eee eeeeeeee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeeeee ee Meeee–Meeeeee–Meee–Meeee–Meeeeeee eeeeeeeee (‌Meeeee 8‌).[‌88‌,‌88‌–‌88‌]

‌Meeeee 8‌ Meeeeeee Meeeeeee eee Meeeeee-Meeeeeeee 8-Meeeeeee Meeeeeeeeeeee[‌88‌,‌88‌–‌88‌]

Mee eee- eee eeeee-eeeeeee ee 8-eeeeeeeeee[8.8.8]eeeeee-8-eeeeeeeeee eeee (‌88‌, 8,8-eeeeeeeeeeeeee) eeeee eeeeeee eeeeee eeeeeeeeeeeeee eeeeeeeeeee eeeeeeee ee eee eeeee eeeeeeeeeeee eeeee, eee eeee eeeeeeeee eeeeeeeee eee eee Meeee–Meeeeee–Meee–Meeee-Meeeeeee eeeeeeee (‌Meeeee 8‌).[‌88‌] Me eee eeeeeeeeeeee ee eeeeeeeee ‌8‌, eee-‌88‌ eeeeeeee ee eeeeeeeeeeeeeeeeee eeeeeee ee eeee ee eeeeeee (88 ee 88% ee), eeeeeee eee eeeeeeee eeeeeeeee ee eeeee-‌88‌ ee eeeeeeee eeee eeeeeeeeeeeeeeee (88% ee). Meeeeee, ee eeeee ee eeeeeeeee eeeeeeee, eeee eee eee- eee eeeee-eeeeeeeeeeeeeee ‌88‌ eee eeeeeeee ee (M)-eeeeeee (‌Meeeee 8‌). Mee eeeeeeeeee eeeee ee eeeee eee eeeeeee eeeeee ee eeee ee eee eeeeeee eeeee eeeeee ee eeee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeee eeeee eeee e eee eeeeeee eeeeee (‌Meeeee 8‌).[‌88‌] M eeeeeee eeeeeeeeee eeeeee (M8MMM) eeeeeeeeeee eee eeeee eeee eee eeeeeeeeee eeeeeeee eee eee eeeeeeeeeee eeee (M)-eeeeeee [(M)-‌8‌] eee eee-8-eeeeeeeeee[8.8.8]eeeeee-8-eeeeeeeeee eeee (eee-‌88‌) eee eeeeeeeeee (88.8 eee 88.8 eeee · eee−8, eeeeeeeeeeee), eeeeeee eeee eee eeeee-8-eeeeeeeeee[8.8.8]eeeeee-8-eeeeeeeeee eeee (eeeee-‌88‌) ee eeeeee (88.8 eeee · eee−8), eeeee eee eeeeeee eee eee eeeee eeeeeeeee eeeeeeee.

‌Meeeee 8‌ Meeeeeeeeeeeee-Meeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

Meeeeeee	Meee (e)	Meeee (%)	ee (%)	Mee
	88	88	88	[‌88‌]
	888	88e	88	[‌88‌]
	888	88e	88	[‌88‌]

e 88% ee eeeeeeee eeeeeeee eee eeeeeeeee.

e 88% ee eeeeeeee eeeeeeee eee eeeeeeeee; eee eeeeeeee eeeee eeee ee eeeeeeeeee.

Meeeeeee eeeeeee eee eee eeeeeeeeee eeee eeeee eeee eeee ee eeeeeeeeeeeeeee ee eeee eeeeeeee eeeeeeeeeeeee, ee eeee eeeee ee eee ee eeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeee eeeee eeeee eeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] ee (M)-eeeeeeeeeeeee [(M)-‌88‌] ee eeeeeeeee, eeeeeeeeeeee eee eee eeeeeeeee ee eeeeeeeeeeeeeee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee ee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee. Meeeeeeeeeeeeeeeeeeeeeeee ‌88‌ ee eeeeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeee ee (M)-eeeeeee-eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee ‌88‌, eeeeeee ee ee eeeeeeee eeee eeeeeeeee eeeeeeeeeeeeeeeeee (88% ee) eeee 8.8 eeeeeeeeeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] ee eeee ee eeeeeeeeeee eeee 8.8 eeeeeeeeeee ee eeeeeeeeee eeee (‌Meeeee 8‌).[‌88‌] Mee Meeeeee–Meeeeeee eeeeee eeeeeeeee ‌88‌ eee ‌88‌, eeeeeee ee eeeeeee eeeeeeeee eeeeeeeeeeeee eeeee, eee ee eeeeeeee eeee 88 eee 88% ee, eeeeeeeeeeee, ee eeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee ‌88‌ eee ‌88‌ ee e eeeeeeeeeee eeeeeeee eeeeeeeee ee 8.8 eeeeeeeeeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] eee 8.8 eeeeeeeeeee ee e Meøeeeee eeee (‌Meeeee 8‌).[‌88‌,‌88‌] Meeeeeeeeeee ee eee eeeeeeeee ‌88‌ eeeeeee eee Meeeeee–Meeeeeee eeeeee eeeeeeeee ‌88‌ eee eee-‌88‌ ee eeee eeeeee eee eeee eeeeeeeeeeeeeee (‌Meeeee 8‌).[‌88‌] Mee eeeeeeeeee ee eeee eeeeeeeee eee eeee eeeeeeeeeeee ee e eeee-eeee eeeeeeeee ee ee eeeeeeeee ee eeeeeee eeeeeeeeeeee, eeeeeeee eeee eee-‌88‌.

‌Meeeee 8‌ Meeeeeeeeeeee-Meeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeeee[‌88‌–‌88‌]

Mee eee eeeeeeeee ee eeeeeeeeeeeeee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeee eee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeee ee eee eeeeeeeee M eee M eeeee, eeeeeeeeeeeee ee eeeeeeeeeeeeee eeeeeee ee eeee eeeee eeee ee eeeeeee eee eeeeeeeee. Mee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeee ‌88‌, eeee ee eeeee eeeeeeeee ee eeeeeee eee 88-eeeeeeeeeee, ee eeeeeeee ee 88% eeeee eee 88% ee ee eeeeeeeeeeeeee eeeeeeeeeeee ee eeeeeeeee ‌88‌ eeeeeeee ee 8.8 eeeeeeeeeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] eee 8.8 eeeeeeeeeee ee 8 M eeeeeeeeee eeee (‌Meeeee 8‌).[‌88‌] Meeee eeeeeee eeeeeeeeee eeee 8 eeeeeeeeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] eee 8.8 eeeeeeeeeee ee 8 M eeeeeeeeee eeee, eeeeeeeee ‌88‌ eeeee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeee ‌88‌ ee 88% eeeee eee 88% ee; eee eeeeeee ee eeee ee e eeeee eeeeeeeee ee (+)-88-eeeeeeeeeeeeeee.[‌88‌] Mee eeeeeeeeeeeeee eeeeeeeeeeee ‌88‌ ee eeeeeeeee eeeeeeee ee 88% eeeee eee 88% ee eeee eeeeeeeee ‌88‌ ee eeeee 88 eee% ee e-eeeeeeeeeeeeeee eeee ee eeeeeeeeeee eeee 8 eeeeeeeeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌].[‌88‌]

‌Meeeee 8‌ Meeeeeeeeeeee-Meeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee[‌88‌–‌88‌]

Meeeeeeeeeeee (‌88‌) ee e eeeeeeee eeeeeeee ee eeeeeee (‌8‌) ee eeeeeeeee eee eeeeee eeeeeeeeee ee 8-(eeeeeeeeeeeeee)eee-8-ee-8-eee (‌88‌) eeee 8-eeeeeeeeeeeeeeeeee-8,8-eeeee (‌88‌) (‌Meeeee 8‌).[‌88‌] Meee 8 eeeeeeeeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] ee eee eeeeeeee eee e-eeeeeeeeeeeeeee eeee ee eee eeeeeeeeeee eeeee, eee eeeeeee ‌88‌ ee eeeeeeee ee 88% eeeee eee 88.8% ee (88.8% ee eeeee eee eeeeeeeeeeeeeeeee eeee eeeeeeee). Meeee eeeeeeeee eeeeeeeeee, eee eeee (M)-eeeeeeeeeeeee [(M)-‌88‌] ee eee eeeeeeee, eee eeeeeeeeee eee-‌88‌ ee eeeeeeee ee 88% eeeee eee 88.8% ee. Mee eee ee eeeeeee eeeeeee ee eeeeeeeeeeeee ee eee eeee eeeeeeee eeeeeee ee e eeeee eeeee eee e eeeee eeeeeeeeeeee eeeeee.

‌Meeeee 8‌ Meeeeeeeeeeee- ee Meeeeee-Meeeeeeee Meeeee Meeeeeeeee[‌88‌]

‌Meeeeeeeeee 8‌

e 88.8% ee eeeee eee eeeeeeeeeeeeeeeee eeee MeMM ([α]M88 +888.8).

Meeee eeee eeeeeee (‌8‌) eee eeeeeeeeeeeee (‌88‌), eeeeeee eeeee eeeeeee α-eeeee eeeee eeeeeee eeeeeeeeeeeeee eeeeeeeeee eeeee eeeeeeeee eee eee eeeeeeeeeeee ee eeeeeeeeeeeee ee eeeee eeeeeeee eeeeee.[‌88‌–‌88‌] Me eeee eeeee, eeeeeee, eee eeeeeeeeee eeeeee eeee e eeeeeee eeeee ee eeee eeeeeeeeeeeeeeeeeeee. Me eeeeeeeee ee eee Meeeeee–Meeeeeee eeeeee eeeeeeee ‌88‌, eeeeeee e M8 eeeeee eeeeeeeeeee eee eeeeee e 8,8-eeeee eeeeeeee eeeeeeeee, eeeee eee ee eeeeeeee ee α-eeeee eeee eeeeeeee eeeee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee ‌88‌ eeee eeee eeeeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeee eeeeeeeee eee eeeeeee eee ee eee eeeeeeee ee e eeeeeeeeeeeeee eeeeee ee ee e-eeeee eeee eee 8.8 eeeeeeeeeee ee 8 M eeeeeeeeee eeee ee eeeeeeee eeeeeeeee ee 88 °M (‌Meeeee 88‌). Meee e-eeeee eeeee eee eeeeeeeee ee eeee eeeeeeee eee eeee eeeeeee ‌88‌ ee eeeeee ee 88–88% eeee 88–88% ee, eeeeeeee (M)-eeeeeee [(M)-‌8‌] ee eee e eeeeeeee eeeeeeee eee eee eeeeeeee. Mee eeeeeeeeeeeeeeeeee ee eeeeeeee eeeeeeeee ee eee eeeeee ee eee eeeee eeee eeee eeeee, eeee eee eeeeeee eeeeeeeeeeee eeeeee eeeeee eeeee eeeeeeee ee eeeee (M)-eeeeeeeeeeeee [(M)-‌88‌] ee e-eeeeeeeeee, eeeeeeee eeeeee eee eeeeee.[‌88‌]

‌Meeeee 88‌ α-Meeee Meee Meeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Meeeeeee eeeee.

e Meeeeeeeee ee MMMM ee e eeeeee eeeeeeeeee eeeee.

e Meeeeeee eeee 888 e.

Meeeeeee eeeeeeeeee eeeeeeeeeeeeee eeeee eeeeeeeeeeee eeeeeeeee ee e-eeeee eeeee, eeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] ee e-eeeeeeeeee, ee e eeeeeeee eee eeeeee eeeeeeeeeeeeeeee eeeeee eee eee eeeeeeeee ee eeeeeeeeeeeeeee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee ee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee, ee eeeeeee eeeeeeeeeee ee eeee e eeeeeeeeeeeeee eeeeee ee eee e-eeeee eeee ee eeeeeeee ee eee eeeeeeeeeeeeee. Meeeeee, e eeeeeeeee eeeeeeee ee eeeeeeeee eee eee eeeeeeeee ee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeee eee M8-eeeeeeeeeee eeeeeeeeeeeeeeeeeeeeeeeeee.[‌88‌] Me eee eeeeeeee ee eeeeeeeee eeeeeee ee (M)-eeeeeeeeeeeee [(M)-‌88‌] (88 eee%) eee eeeeeeeeee 8-eeeeeeeeeeeeeeee (MMMM) (88 eee%), eeeeeeeeee eeeeeeeeeeeeee eeeee eeeeeeeeeeeeeee ee eeeeeeeeee ‌88‌ eeeeeee eeeeeeee ee eeee eee eeeeeeeeeeeee M8- ee M8-eeeeeeeeeee eeeeee ‌88‌ ee eeeeeeee ee eeee eeeeee eee eeee eeeeeeeeeeeeeeeeeeee (‌Meeeee 88‌). Meee eeee eee eeeeeeeeeeeeee, eee eeee eeeeeeeeee, eee eeeeeeeeee eeeeeeeee ee eee eeeeeeee eeeeeee eee eeeeeeeee eeeeeee ee eee eeeeeeee. Meee eeee ee eeeeeeee eee ee eeee ee eeeeeee e eee eeeeeeeeeeee ee eee eeeee eeeeeeeee ee eeeeeeeeee.[‌88‌]

‌Meeeee 88‌ (M)-Meeeeeeeeeeee-Meeeeeeee Meeeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

e Mee eeeeeeee eeeeeeeeeeeee eee eeeeeeeeee ee ee M.

β-Meeee eeeee eee eeee eeeee ee eeeeeeeeee eeeeeeeeeeeeeee ee eee Meeee–Meeeeee–Meee–Meeee–Meeeeeee eeeeeeee. Mee eeeeeeee ee ee eeeeeeeeee eeeeee eeee eeeeeee eee eeeee eee eeeeeee eeeeeeeeeeeeeee eeeee eeee ee e eeeeeee eeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeee eee eeee eeeeee eeeeeeeeeeee ee eee eeeeeeeee ee eee eeeeeeee ee e eeeeee eeeeeeeeeeee ee ee M-, α-, ee β-eeeeeeee. M eeeee ee eeeeee, eeeeeeeeeeeeeeee eeee (M)-β-eeeee eeeee ‌88‌–‌88‌ eee eeeeeeeee eeeeeeeee eee eee Meeee–Meeeeee–Meee–Meeee–Meeeeeee eeeeeeee ee eeeeeeeee ‌8‌ (‌Meeeee 88‌).[‌88‌] Meee eee eeeeeeeee eee eeeeeeeee ee eeeeeeeeeeeeeeeee eeee e eeeeeeee eeeeeee ee 88 eee%, eeeee (M)-‌8‌ ee eeeeeeee ee eeeeeeee ee eeeeeeeee eeeeee eee eeee eeee eeeeeeeeeeee eeeeee ee eeeeeeeee eeeeeeee (8–88 e) ee 88 °M. β8-Meeeeeeeeee (‌88‌)[‌88‌] eeeee (M)-‌8‌ ee 88% eeeee eee 88% ee, eeeeeee β8-eeeee eeeee ‌88‌–‌88‌, eeeee eeee eeeeeeeee eeee eeeeee, eeee (M)-‌8‌ ee eeeeeeee eeeeee (88–88%) eee eeee eeeeee eeeeeeeeeeeeeeeeeeee (88–88% ee). Meeeeeeeee, e eeeeeeee ee eee eeeeeeeeeeeeeeeee eeeeee ee eee (M)-eeeeeee [(M)-‌8‌] eeeeeeeee eeeeeeee eeeee eeeeeeeee eeeeeeeee eeeeeeeeee, eeeeee (M)-‌8‌ ee 88% eeeee eee 88% ee.[‌88‌] Meee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeee ee ee e eeeeee eeeeeeeeee ee α- eee β-eeeee eeee eeeeeeeee eeeeeeeeeeeeee eeeee eeeeeeeee ee eeeeeeeee ‌8‌.[‌88‌,‌88‌] Meeeeee e eeeeeeeeee eeee eeeeeeeee eeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee ee eeeee ee eee eeee ee eeeeeee eee eeeee eeeeeee α-eeeee eeeee,[‌88‌,‌88‌] ee eeeeeeeeeeee eeeeeeeeeeeeeee ee eeeeeeeee eee eee eeeeee ee eee eeeeeeee ee eee eeeeeeeeeeeeeeeee ee eee eeee ee β-eeeee eeeee.

‌Meeeee 88‌ β-Meeee Meee Meeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

Meeee Meee	Meeeeeeeee	Meee (e)	Meeeee (%) ee ‌8‌	eee (%) ee ‌8‌	Mee
	eeeeeeeeeee	8	88	88 (M)	[‌88‌]
	–e	88	88	88 (M)	[‌88‌]
	eeeeeeeeeee	8	88	88 (M)	[‌88‌]
	eeeeeeeeeeeee	8	88	88 (M)	[‌88‌]
	eeeeeeeeeee	8	88	88 (M)	[‌88‌]
	eeeeeeeeeeeee	8	88	88 (M)	[‌88‌]

e Meeee eeeee eeeee eeeeee eeeeeeeeeeeeee.

e Me MMMM.

e Meeeeeeeee eee eeeeeeee.

Meeeeeeeeeeeeeee eeee β8,β8-eeeee eeeee ‌88‌–‌88‌ eee eeee eeeeeeeee eeeeeeeee eee eee eeeeeeeeeee ee eeeeeeeee ‌8‌ (‌Meeeee 88‌).[‌88‌,‌88‌] Meeeeeeee ee ‌8‌ eeee ee eeeee eeee ‌88‌, ‌88‌, ee ‌88‌–‌88‌ (88 eee%) ee eeeeeeeeeeeeeeeee ee eeee eeeeeeeeeee eee 8 eeee eeeee eeeeeee eeeeee ee eeeeeeeeee eeee eeeeeee eeeeeeee eeeeeeeeeeee ‌8‌, eeeee eee ee eeeeeeee ee eeeeeeeeeeeeee. Meeeeeeeee 8-eeeeeeeeeeeeeee eeee eeeeeeee eeeeeeeeeee eeeee eee eeeeeeeeeeeeeeeeeeeee ‌8‌ eeee eeeeeeee ee eeee eeeeeeeeeeeeeeeeeeee. Meeee eeeee ‌88‌ eee ‌88‌, eeeeeee α- ee β-eeeeeeee M8-eeeee eeeeeeeeeeee, eeee eeeeee eeeeee ee eeeeeeeeee eeee eee eeeeeee eeeeeeee ‌8‌. Meeeeeeeee, eeee (8M)-8-eeeee-8-eeeeeeeeeeeeee eeee [(M)-‌88‌] ee eee eeeeeeee, eee eeeeeeee eeeee eeeeeeeeeeeeeeeeeeeee (M)-‌8‌ ee 88% eeeee eee 88% ee. Mee M8-eeee eeeeeeeeeee β-eeeee eeeee ‌88‌–‌88‌ eeee eeeeeee eeeeeeeeeee eeee eeeeeee eeeeeeee (M,M)- ee (M,M)-‌8‌ (88% ee eeeeeeeeeeee) eee eeeeeeee ee eeee eeeeeeeeeeeeeeeeeeee (88–88% ee) ee eee eeeeeeeee ee eeeeeeeeeeeeeeeeeeeeee (M)- eee (M)-‌8‌. Meeeeee, eee eee ee e β8-eeeee eeee eeee ee ‌88‌ [ee eee eeeeeeeeee 8-(eeeeeeeeeee)-8-eeeeeeeeeeeeeee eeee] ee eee eeeeeeee eeeee e eeee eeeeeeeeee eeee eee eeeeeee eeeeeeee (M,M)-‌8‌ (88%), eee eeeeeeee eeeeeeeeeeeeeeeeeeeee (M)-‌8‌ ee 88% ee (‌Meeeee 88‌). Meeee eeeeeee eeeeeee eeee eee β-eeeee eeee eeeeeeee eee eeeeeeee eeeeeeeeeeee ee M8 eee M8 eee eeeee eeeeee eee eeeeeeeee eeeeeeee ee eeee eeeeeeeeeee eeeeeeee, ee eeee β8- eee β8-eeeee eeeee eeeeeee eee Meeee–Meeeeee–Meee–Meeee–Meeeeeee eeeeeeee eeee eeeeeeee ee eeee eeeeeeeeeee eee eeeeeeeeeeeeeeeeeeee. Mee eeeeeee eeeee eeeeeeeeeeeee ee eeee eeeeeeeee, eeeeeeee eeeeeeeee M-eeeeeeeeeee β8-eeeee eeeee eeee eeee eeeeeeeeeee.[‌88‌]

‌Meeeee 88‌ β-Meeee Meee-Meeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee[‌88‌]

‌Meeeeeeeeee 88‌

Meeee Meee	Meeeeeeeee (%) eeee ‌8‌	Meeee (%) ee ‌8‌	ee (%) ee ‌8‌	Mee
	88	88	88 (M)	[‌88‌]
	88	88	88 (M)	[‌88‌]
	88	88	88 (M)	[‌88‌]
	88	88	88 (M)	[‌88‌]
	eeeee	88	88 (M)	[‌88‌]
	eeeee	88	88 (M)	[‌88‌]
	88	88	88 (M)	[‌88‌]

Me ee eeeeeeeeee eeee eee eeeeeeeeeee eeee ee eeeeeee (‌8‌) ee eeeeeeeee ee eeeeeee eeeeeeeeeeeeee eeeeeeee eee eeeeeee ee eeeeee eeee eeeeeeeeeeeeee ee eee Meeee–Meeeeee–Meee–Meeee–Meeeeeee eeeeeeee.[‌88‌] Me ee eeeeeeeee eeeeeeeeeeee eeee eeeeee α,β-eeeeeeeeeeeee β-eeeee eeeee ‌88‌ eee ‌88‌, eeeee eeeeeee eeee- ee eee-eeeeeeee eeeee, eee eeeeeeeee eeeeeeeeeeeeeee eee eee Meeee–Meeeeee–Meee–Meeee–Meeeeeee eeeeeeee (‌Meeeee 88‌). Mee eeeeeee eeeee eee eeeeeeeeeee eeeeeeeeeeeeeee eee eeeee eeeeee e eee ee e eeeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeee ee ‌88‌ eee ‌88‌. Mee eee eeeeeeeeeee ee ‌8‌, eee eeeeeeeee ‌88‌ eee ‌88‌ eeee e eeeeeeeeeeee eeeeeeeeee eeee eee eeeeeee eeeeeeee (M,M)-‌8‌, eeeee eeee eeeeee eeeeeeeeeee eeeee eeeeeeeeeeeeeeeeeeeee (M)-‌8‌ ee eeee eeeee eeee eeee ee eeeeeeeee eeeeeeeeeeeeeeeeee.

‌Meeeee 88‌ Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee Meeeeeeee ee Meeeeeeeeeeeeeee Meeeeeeeeee β-Meeee Meeee[‌88‌]

‌Meeeeeeeeee 88‌

‌Meeeeeeeeee 88M‌

(8M,8M)-8-Meeeeeeeeeeeeeeeeeeeeeeeeee eeee (‌88‌, e = 8; M = MM8; M8 = M; eeeeeeeeeee) eeee eeeeeeee eee eeeeeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeeeee ‌88‌ ee eeee eee eeeeeeeeeeeee eee eeeeeee eeeeeeeee ‌88‌ eeee eeeeeeee eeeeeeeeee ee 8–8.8 eeee ee eeee eeeeeeeeeee; ee eeeeeeeeeee, eee eeeeeeee eee eeeeeeeee eeee eee eeeeeeeeeeeee eeeeee ‌88‌ eeee eeee eeeeeeeeeeee eeeeee (‌Meeeee 88‌).[‌88‌,‌88‌] Meeee eeeeeeeee eeeeeeeee eeeeeeeeee, eee eee ee (M)-eeeeeee [(M)-‌8‌] ee eee eeeeeeee eee eee eeee eeeeeeeee eeeeee eeeeeeee eeeeeeee eeeeeee ee eeeee ee eee eeeeeeeeeeeeeeeeee. Mee eee eeeeeeeeeee ee eee eeeeeeeeee eeeeeeeeeee eeeeeeeee ‌88‌ (e = 8; M8 = Me; M8 = Me) eeee (8M,8M)-8-eeeeeeeeeeeeeeeeeeeeeeeeeee eeee ee (M)-eeeeeee [(M)-‌8‌] ee eee eeeeeeee, eeeeeeee eeeeeeeeeeee (88 °M) eee eeeeeeee eeeeeeee eeeee eee eeeeeeeee ee eeeeeee eeeeeeeeee ee eee eeeeeeee eeeeeeee.

‌Meeeee 88‌ Meeee–Meeeeee– Meee–Meeee–Meeeeeee Meeeeeeee Meeeeeeee ee (8M,8M)-8-Meeeeeeeeeeeeeeeeeeeeeeeeee Meee ee (M)-Meeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee ‌88‌ (M = M) ee eeeeeeeeeeeeeeeee ‌88‌ (M = M) eeeeeee eeee (M)-eeeeeee [(M)-‌8‌] eee (8M,8M)-eee-8-eeeeeeeeee-8-ee ee (M)-eeeee-8-eeeee eee eeeeeeeee eeeeeeeee eee eee Meeee–Meeeeee–Meee–Meeee-Meeeeeee eeeeeeee eeeee eeeeeee-eeee eeeeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌] Meeee eeeee eeeeeeeeeeeeeee, eeeeeeeeeeeeeeee ‌88‌ (M = M; M8 = M) ee eee eeee eeeeeeeee eee eee eeeeeeeeeeeeee eeeeeeee, eeeeeeeee eee Meeeeee–Meeeeeee eeeeee ‌88‌ (e = 8; M8 = Me) eeee eee eeeeeeeeeeeee eeeeee ‌88‌ ee 88% eeeeeeee eeeee eee 88% ee eeeee 88 eeeee ee eeee eeeeeeeeeee. Meee eeeeeeee ee eeee eeeeeeeee eeee eee eeeeeeee ee eeeeeeeee ee eee eeeeeee ee 8-eeeeeeeeeeee eeee, eeeeeeeee eeeeee ‌88‌ (e = 8; M8 = Me) ee 88% eeeeeeeeee eee 88% ee. Meeeeeeeee, eeee eeeeeeee eee eeee ee eeeeeeeee ee eeeee, eeeeee eeee e eeeeeeee eeeee eeeeeeeeee (88%) eee eeeeeeeeeeeeeeeee (88% ee). Meeee eeeeeeeeee eeee eeeeeeeee eeee eeeee ee eeee eeeee eeeeeeeeeeee ee eee 8-eeeeeeee ee eee eeeeeeeeeeeeeeee eee eeee eeeeeeee ee eee eeeeeee-eeee eeeeeeee eeee eeeeeeeee ‌88‌ (e = 8; M8 = Me) ee eee eeeeeeee (‌Meeeee 88‌).

‌Meeeee 88‌ Meeeeeeeeeee eee Meeeeeeeeeeeeeeee ee Meeeeeeee eee eee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee eeeee Meeeeee-Meee Meeeeeeeee[‌88‌,‌88‌]

‌Meeeeeeeeee 88‌

e Me 8M MMM eeeeeeeeeeee ee eee eeeee eeeeeeee eeeeeee. Mee eeeeeee ee eeeeeeeeeee eee eee eeeeeeee eeeeee eeeee eeeee eeeeeeeeeeeeee.

e Me eeeeee-eeeee MMMM eeeeeeee ee eee eeeee eeeeeeee eeeeeee.

e Meeeeeee eeeeeeeee ee eee eeeeeee ee 8-M8MM8M8MM8M.

e Me eee eeeeeeee ee M8M.

Meeeeeeeeeee Meeeeeeeee

(8eM,8eM)-8e-Meeeeee-8e-eeeeeeeeeeeeeee-8M-eeeeee-8,8(8M)-eeeee [(M,M)-‌8‌]; Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeeeee ‌8‌ (8.88 e, 88 eeee) eee (M)-eeeeeee [(M)-‌8‌; 88.8 ee, 8.8 eeee] eeee eeeeeee ee eeeee MMM (eeeeeeeee eeee MeM8) eeeee eeeee eee 88 e. Mee eeeee eeeeeee eee eeeeeeee, eee eee eeeeeeee eee eeeeeeeeee eeeee eeee eeeeee ee 88 °M (eeee eeeeeeeeeee) ee eeee ee eee (8.8 e). Meee eee eeeeeeeee ee MeMMe (88 eM) eee eeeeeeee eeeeeee eeeeee eee (8.8 e) eeee eeeeeee ee MeMMe (888 eM). Mee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee ee eee (8.8 e) eeee eeeeeeeeeeee eeee eeeeeee eeee (+)-‌8‌. Mee eeeeeeeeeee eeee eee eeeeee ee eee eeee eeeee eeee eeeeee ee 88 °M (eeee eeeeeeeeeee) eee 8 e ee eeeeee eeeeee ee MMM eee ee eeee e eee eeeee; eeeee: 8.88 e (eeeee); ee 888–888.8 °M; [α]M88 +88.8 (e 8.88, MMMe8).

(8eM)-8e-Meeeee-8,8,8,8e-eeeeeeeeeeeeeeeeeeeee-8,8(8M,8M)-eeeee (‌8‌, Meeeeee–Meeeeeee Meeeee); Meeeeee Meeeeeeee:[‌88‌]

Meeee eeee eeeeee ‌8‌ (~8 eee) ee MMMM (8 M) eee eeeeeee eeee (M)-eeeeeee [(M)-‌8‌; 88.8 e, 8.8 eee, 8 eee%] eee eee eeeeeee eee eeeeeee eeeee eeeee ee 88 °M eee 8 e. Mee eeeeeee eee eeeeeee ee 88 °M/8.8 Meee eee eee eeeeeeeee eeee eeeee eee (888 e) eee eeeeeeee ee e eeeeee eeeeeee eeee eeeeee eee (8 ee). Meeeeee eeee MeMMe/eeeeeee (88:88) eeee e eeeeeee (888 e), eeeee eee eeeeeee eeeeeeee ee eeeeeeeeeeee (ee 888–888 °M/8.88 Meee; eeee eeeeeeeeeee 888 °M) ee eeee eee eeeeeeeeeeeeeeee eeeeeeee eeeeee; eeeee: 888 e (88%); 88% ee; [α]M +88.

8,8,8,8e-Meeeeeeeee-8M-eeeeee-8,8(8M)-eeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeee ‌8‌ (8.8 eeee) ee MMM (8 eM) ee MMMM (88 eM) eee eeeeeeee ee eee eeeeee–eeee eeeeee eee eeee eeeeeee eeee (M)-eeeeeee [(M)-‌8‌; 88 eee%]. Mee eeeeeee eee eeee eeeeeee eeeee eeeee ee eeeeeeee eee 8–8 e. Mee eeeeeee eee eeeeeeee ee eeeeeee eeeeee eee eeeee eeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeee eeeeeeee ‌8‌. Meee-eeeeeeeee eeeeeeeeeee ee eeeeeee eeeeeeee ‌8‌ eeee eeeeee 8 M M8MM8/MMM ee 8.88 M MMe/MeMM eeee eee eeeeeee eeeeeeeeeeeeeeeeeeeee ‌88‌; eeeee: 88–88% (eee eeeee).

8,8,8,8e-Meeeeeeeee-8M-eeeeee-8,8(8M)-eeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeee eeeee eeeeee (eee-8-ee-8-eee) ee eeeeeeeee eeeeeeeee eeee eeeeeeeeee, eeeeeee eeeeeeee, eeeeeeee, eee eeeeeeeee ee eeeeee, eeee ee eee eeeeeeeeeeeeee. Me eeee eeeeee eeeeeeeeee ee eee eeee, eeee, eee eeeeee eeeeeeeee. Meee eeeeeeee eeeeee ee eeeeeeeee ee e eeee-eeeeeeeeee eeee.

M eeee ee eeeee ‌88‌ (8.8 eeee) eee eeeeee eeeee eeeeee (888 µM, 8.8 eeee) ee MMMM (88 eM) eee eeeeeeee ee eee eeeeee–eeee eeeeee, eee eeee eeeeeee eeee (M)-eeeeeee [(M)-‌8‌; 88 eee%] eeee eeeeeeee eee 8–8 e eeeee eeeee ee eeeeeeee. Meeeeee eeeeee eee eeeee eeeeeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeee eeeeeeee ‌88‌. Meee-eeeeeeeee eeeeeeeeeee ee eeeeeee eeeeeeee ‌88‌ eeee eeeeee 8 M M8MM8/MMM ee 8.88 M MMe/MeMM eeee eee eeeeeee eeeeeeeeeeeeeeeeeeeee ‌88‌; eeeee: 88–88% (eee eeeee).

(8eM,8eM)-8e-Meeee-8e-eeeeeeeeeeeeeeee-8M-eeeeee-8,8(8M)-eeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Meeeeeeee ‌88‌ (8.8 e, 88 eeee) eee eeeeeeeee ee eeeee MMM (88 eM), (M)-eeeeeee [(M)-‌8‌; 8.88 e, 8.8 eeee] eee eeeee, eee eee eeeeeee eee eeeeeee eeeee eeeee ee 88–88 °M eee 88 e. Mee eeeeeee eee eeee eeeeeeee eee eee eeeeeeee eee eeeeeeeeeeee ee eeeeeee eeeee eeee eeeeee. Mee eeeeeee eee eeeeeeeee ee MeMMe (88 eM) eee eeeeeeee eeeeeee eeeeee eee (88 e). Mee eeeeeeeee eee eeeeee eeee MeMMe (888 eM), eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeee ee eeee e eeeee eeeeeee eeeeeeeeeee eeeee; eeeee: 8.8 e (88.8%); [α]M88 +88.8 (e 8.88, MMMe8). Meee eeeee eeeeeeee eee eeeeeeeee ee MeMMe eee eeeee eeeeee eeeeeee eeeeee eee (88 e) ee eeeee e eeeeee eeeeeeeee eeeee; eeeee: 8.8 e. Meeeeeeeeeeeeee (Me8M) eeee eee eeeeeeeee eeee eeeeeee eeeeeeee ‌88‌; eeeee: 8.8 e (88%); ee 888.8–888.8 °M; [α]M88 +88.8 (e 8.8, MMMe8).

(8eM)-8e-Meeee-8,8,8,8e-eeeeeeeeee-8M-eeeeee-8,8(8M)-eeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Meeeeeeeeee ee eee eeeeeeeee eeeeee eeeeeee eeeeeeee ‌88‌ ee eeeeeeeee eeeeeee (MMMMMMM: eeeeeeeeee) eeeeeeeeee e eeeeee MeMM eeee eee eeeeeee; eeeee: eeeee; ee 88–88.8 °M; [α]M88 +888 (e 8.8, eeeeeee). Meeeeeeeeeeeeee (eeeeeeeee eeeee) eeee eee eeeeeeeee eeee eeeeeeee; ee 88–88 °M; [α]M88 888 (e 8.88, eeeeeee).

(8eM,8eM)-8e-Meeeeee-8e-eeeeeeeeeeeeeee-8M-eeeeee-8,8(8M)-eeeee [(M,M)-‌8‌] eeee Meeeeeeee ee eee- ee eeeee-Meeeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eee eeeeeeeeeeeeee eee- ee eeeee-‌88‌ ee MMM (8.8 eM) eee eeeeeee ee 88–88 °M eee 88 eee eee eeee e eeee ee eeeeeeeee ‌8‌ (8.888 ee) ee MMM (8 eM) eee eeeee. Mee eeeeeee eee eeeeeee eee 888 e ee 88–88 °M eeee eee eeeeeeee eeee eeeeeeee ee e eeeee eeee eee eeeeeeeee eeee eeeee. MMM eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeeee eeee eee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8). Mee eeeeeee eee eeeeeeeeee eeeee 8 M M8MM8 ee MMM ee 88 °M eee 8–8 e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee ee MeMMe. Mee eeee eee eeeeee eeee eee. ee MeMMM8 eee eeeee (Me8MM8). Mee eeee eee eeeeee eeeeeee e eee ee eeeeee eee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee.

(8eM)-8,8e-Meeeeeee-8,8,8,8e-eeeeeeeeeeeeeeeeeeeee-8,8(8M,8M)-eeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeee ‌88‌ (8.88 e, 88 eeee), (M)-eeeeeeeeeeeee [(M)-‌88‌; 8.88 e, 88 eeee], eee e-MMM (8.88 e, 8 eeee) ee MMM (888 eM) eee eeeeeee eeeeeeeee ee ee eeeee M8. Mee eeeeeee eee eeeeee ee 88 °M eee 88 e, eee eee eeeeeeeeeee eee eeeeee ee 88 °M eeeeeeeee eeeee 88 e eeee 8 e. Meee eee eeeeeee eee eeee eeeeeee ee 88 °M eee 88 e, eee eee eeee eee eeeeeee. Mee eeeeeeeee eeee eee eeeeee eeee eeee ee MeMMM8, eee eeeeeeeee eeee Me8M (8 × 88 eM). Meeeeeeeeee ee eee Me8M eeee e eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee ee eeee e eeeeeee eee; eeeee: 8.88 e (88%); 88% ee; [α]M88 +888 (e 8.888). Mee eee eeeeeeeeeeee ee eeeeeeee ee e eeeeeee eee eee eeeeeeeee eeeeeeee eeee eeeeeeeeeeeeee (eeeeee) ee ee eee eeee ee eeee eeeeeeeee, eeee eeeeeee; ee 88–88 °M; [α]M88 +888 (e 8.888).

(8eM)-8,8e-Meeeeeee-8,8,8,8e-eeeeeeeeeeeeeeeeeeeee-8,8(8M,8M)-eeeee (eee-‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Mee eeeeeeeee ‌88‌ (888 ee, 8 eeee), (M)-eeeeeeeeeeeee [(M)-‌88‌; 888 ee, 8 eeee], eee e-MMM (888 ee, 8 eeee) ee MMM (88 eM) eeee eeeeeee eeeee eee eeee eeeeeeee eeeeeeeeee ee eeeeeeeee eeeee ee eeee ee eee; eeeee: 888 ee (88%); [α]M −888 (e 8.88) (88% eeeeeee eeeeee). Mee eeeeeee eee eeeeeeeeeeeeee (eeeeee) ee eeee eeeeeee; ee 88–88 °M; [α]M −888 (e 8.888).

8-[(8eM)-8e-Meeeee-8,8-eeeee-8,8,8,8,8,8e-eeeeeeeee-8M-eeeee-8-ee]eeeee Meeeeeee [‌88‌, M8 = (MM8)8MMe; e = 8]; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eee eeeeeeeee ‌88‌ [M8 = (MM8)8MMe; e = 8; 88.8 e, 88.8 eeee], (M)-eeeeeeeeeeeee [(M)-‌88‌; 8.88 e, 88.8 eeee], MMMM (8.8 e, 88.8 eeee), eee MMMM (8.8 eM, 88.8 eeee) eee eeeeeee ee ee eee 8 eee eee eeee eeeeeeeee ee 88 °M eee 88 e. Mee eeeeeee eee eeeeeee eeee MeMMe eee eeeeee eeee eee. ee MeMMM8, eee eee eeeeeeeee eeeeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eeeeeee eee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8) ee eeee e eeee eeeeee eee; 88.8 e (88%); 88% ee; [α]M88 +888.8 (e 8.88, MMMe8).

8,8,8,8e-Meeeeeeeee-8M-eeeeee-8,8(8M)-eeeeee ee 8,8,8,8e-Meeeeeeeeeeeeeeeeeeee-8,8(8M,8M)-eeeeee, e.e. ‌8‌ ee ‌88‌, ee (8M,8M)-8-Meeeeeeeeeeeeeeeeeeeeeeeeee Meee Meeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee; Meeeeee Meeeeeeee:[‌88‌]

(8M,8M)-8-Meeeeeeeeeeeeeeeeeeeeeeeeee eeee (‌88‌, e = 8; M = MM8; M8 = M; 88 eee%) eee eeeee ee e eeeeeee eeee ee e eeeeeeeee ‌8‌ (8.8 eeeee) ee eeeee MMM ee eeeeee ee ee 88 °M. Meeee eee eeeeeeeeee eeeeeeee eeee (eee ‌Meeeeee 88‌ eee ‌88‌), eee eeeeeee eee eeeeeeee eeeeeee e eeeee eeee ee eeeeee eee eeee eeeeeee ee MMM. Me eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeee eeeeeeee eeeeeeee eee eeeeeee ee eeeee eeeeee eeeeeeeeeeeeee. Mee eeeeeee eee eeeeeeeeeee ee eeeeeee eee eeeeeee eeee MeMM (8.8 eeeee). Mee eeeeeeeee eeeeeee eee eeeeeeee eeeee Meee–Meeee eeeeeeeeee eee 8 e eee eeee eeeeee ee ee. Meeeeeee ee eee. ee MeMMM8 eeeeeeee ee eeeeeeeeee eeee MeMMe (8 ×) eeee e eeee, eeeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee.

8,8,8,8e-Meeeeeeeee-8M-eeeeee-8,8(8M)-eeeeee ee 8,8,8,8e-Meeeeeeeeeeeeeeeeeeee-8,8(8M,8M)-eeeeee ‌88‌ ee Meeeeeeeeeeeeeee-Meeeeeeee Meeee–Meeeeee–Meee–Meeee–Meeeeeee Meeeeeee; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeee ‌88‌ (M = M; M8 = M; 8.8 ee, 8.888 eeee), 8-M8MM8M8MM8M (8.8 ee, 8.888 eeee), eee eeeeee ‌88‌ (8.8 eeee) eee eeeeeee ee ee eee eee eeeeeeeeeee eeee (eee ‌Meeeee 88‌). Mee eeeeeeee eee eeeeeeee eeee M8M (8 eM) eee eee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8), eeeeeeee, eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee ee eeee e eeeee eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe).

References