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2.1.6.1 Reactions Involving Cyclic α,β-Unsaturated Carbonyl Compounds as Dipolarophiles

DOI: 10.1055/sos-SD-211-00033

Raghunathan, R.; Purushothaman, S.Science of Synthesis: Multicomponent Reactions, (20142212.

1,3-Dipolar cycloadditions of azomethine ylides with α,β-unsaturated carbonyl compounds as dipolarophiles represent an important methodology for the construction of spiro-fused pyrrolidine ring systems, which are prevalent in a variety of biologically active compounds. The azomethine ylides (e.g., 3) generated from isatin (1; 1H-indole-2,3-dione) (and derivatives thereof) and cyclic and acyclic α-amino acids, such as sarcosine (2; N-methylglycine) (Scheme 2), are considered to be important since their cycloaddition to alkenes leads to the formation of spiro[indoline-3,2′-pyrrolidin]-2-ones, which form the basic building units of several natural products.[‌8‌‌11‌]

Meeeee 8 Meeeeeeeee ee ee Meeeeeeeee Meeee eeee Meeeee eee Meeeeeeee

Meeeeeeeeeeeee [8 + 8]-eeeeeeeeeeeee eeeeeeeee eeee e eee eeee ee eee eeeeeeeee ee eeee-eeeeeeee eeeeeeeeeeee. 8,8-Meeeeee eeeeeeeeeeeee ee eeeeeeeeee eeeeee eeee eeeeeeeeeeeeee ee e eeeeeeee eeeeee eee eee eeeeeeeeeeee ee eeeeeeeeeeee eeeeee eeee-eeeeeeee eeeeeeeeeee eeeeeeeeeee eeee eeeeeee. Mee eeeeeeeeee eeeeee eeeeeeeee eeee eeeeeee eeeeeeeeeee eeeeeee (8) eee eeeeeeeee (8) eeeeeee e eeee [8 + 8]-eeeeeeeeeeeee eeeeeeee eeee 8-(8M-eeeeee-8-eeeeeeee)-8-eeeeeeeeeeeeeeeeeee (8) ee e eeeeeeeeeeeee ee eeee e eeeeee eeeeee ee eee eeeee-eeeee eeeeeeeeeee eeeeeeee 8. Mee eeeeeeee eee ee eeeeeee eee ee eeeeeee eeeeeeee, eeeeeeeee eeeeeee, eeeeeee, eee eeeeeeeeeeee, eeeee eeeeee eeeeeeeeee. Meee eeeeeee eee eeeeeeee eeeee eeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee ee Meeee[eeeeeeee-8,8′-eeeeeeeeee]-8-eeee[‌88‌]

Meeeeeeeeee 8

M8 M8 Meee (eee) Meeee (%) Mee
M M 88 88 [‌88‌]
Me M 88 88 [‌88‌]
Me M 88 88 [‌88‌]
M MM8MMMM8 88 88 [‌88‌]
M Me 88 88 [‌88‌]
M MM8M≡MM 888 88 [‌88‌]

Mee eeeeeeeeee eeeeee eeeeeeeee eeee eeeeeee 8 eee eeeeeeeee (8) eeeee eeee 8-eeeeee-8-eeeeeeeeee-8-eeee 8 ee eeeeeee eeeee eeeeee ee eeee eee eeeeeeee 8, eeeeeee eee eeee eeeeeeee eeeeeee eee ee eeeeeeee eeeeeee eee eeeeeeeeeeee eeeeeee 88, eeeeeeeeee ee e eeeeee ee eeeeeeeeeeee eeeeee ee eeeeeeee ee eee eeeeee eeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee ee Meeee-Meeee [8]Meeeeeeeeee[8,8-e]eeeeeeeeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 M8 Meeeee (%) Mee
M M M 88 [‌88‌]
M M MMe 88 [‌88‌]
M Me M 88 [‌88‌]
Me M M 88 [‌88‌]
Me M MMe 88 [‌88‌]
Me Me M 88 [‌88‌]

e Meeee ee eeee eeeeeee eeeee eeeeeeeeeeeeeeeee eeee eeeeeeeeeeee.

Meeeeeeeeee 8M

M8 M8 M8 Meeeee (%) Mee
M M M 88 [‌88‌]
M M MMe 88 [‌88‌]
M Me M 88 [‌88‌]
Me M M 88 [‌88‌]
Me M MMe 88 [‌88‌]
Me Me M 88 [‌88‌]

e Meeee ee eeee eeeeeee eeeee eeeeeeeeeeeeeeeee eeee eeeeeeee.

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

Meeeee 8 Meeeeeeee ee Meeeeeeeeeeee Meeee-Meeee Meeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 8

Me8 Meee (e) Meeee (%) Meeee Meeee (%) Mee
88 88
Me 88 88 88 88 [‌88‌]
8-Mee 88 88 88 88 [‌88‌]
8-MeM8M8 8 88 88 88 [‌88‌]
8-MeM8M8 8 88 88 88 [‌88‌]

Mee 8,8-eeeeee (eeeeeeeeee eeeee) eeeeeeeee eeee eee eeeeeeeeeeeeeee eeeeeeeeeeee ee eeeeee (8) eee eeeeeeeee (8) eeeeee eeee eeeeeeeeeeeeee 88, eeeeeeeeee ee eeeeeeeee eeeeee eeee, ee eeeeee eeeeeee-eeeee eeeeeeeeeeee 88 (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeee[eeeeeeeeeeeeeeeeeeeeeeeeeeeeee]eeeeee eeee 8-Meeeeeeeeeeeeeeeeeeeeeeee eee ee Meeeeeeeee Meeee[‌88‌]

Meeeeeeeeee 8

Me8 Meeee (%) Mee
Me 88 [‌88‌]
8-Mee 88 [‌88‌]
8-MeMM8M8 88 [‌88‌]
8-MeM8M8 88 [‌88‌]
8,8,8-(MeM)8M8M8 88 [‌88‌]

Meeee eeeeeee-eeeee eeeeeeeeeeeeee 88 eee eeeeeeee eeeeeee eee eeeeeeee ee eeeeeeeeee eeeeee eeeeeeeee eeee eeeeee (8) eee e-eeeeeee (88) eeee eeeeeee eeeeeeeeeeeeee 88 (Meeeee 8).[‌88‌] Mee eee-eee, eeeee-eeeeeeeee eeeeeeee ee eeee eeeeeee eee ee eeeeeeeeeeeeeee ee e eeeeeee ee 8 eeeeeeeeee ee eeeeee, 8 eeeeeeeeee ee e-eeeeeee, eee 8 eeeeeeeeee ee eee eeeeeeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeee ee eeeeee eee.

Meeeee 8 Meeeeeeee ee Meeee-Meeee Meeeeeeeeeeeee eeee Meeeee, Meeeeee, eee 8-(Meeeeeeeeeeeeeee)eeeeeee[‌88‌]

Meeeeeeeeee 8

Me8 Meeeeeeeee Meee (e) Meeee (%) Mee
Me MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-MeM8M8 MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-Mee MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-MeMM8M8 MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-MeM8M8 MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]

Meeeeeeee ee eeeee eeeeeee[eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee]eeeeee 88 ee eeeeeeeeeeee ee e eee-eee eeeeeeee ee eeeeeeeeeeeeee-8,8-eeeee (88), eeeeeeeee (8), eee eeeeeee eeee-eeeeeeeeeee (M)-8-eeeeeeeee-8-eeeeeeeeeeeee 88. Mee eeeeeeee ee eeeee 88 eeee eeeeeeeee eeeeeeeee ee eeeeeeeeeeee eeeeeeeeee eeeee ee eeeeeeeeeeeeeee eeeeeeeeeeee, eee eeee eeeee eeeeeeeee eeeeeeeeeeeee eeeeee eee eeeeeeeee eeee ee eee eeeeeeeeeee eeeeeeeeeee ee eeee eeeeeeeeeeee 88 ee eeee eeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeee[eeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee]eeeeee[‌88‌]

Meeeeeeeeee 8

Me8 Meeeeeeeee Meee Meeee (%) Mee
Me eeeeeee/MeMM, eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-Mee eeeeeee/MeMM, eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-MeMM8M8 eeeeeee/MeMM, eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-MeM8M8 eeeeeee/MeMM, eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-MeM8M8 eeeeeee/MeMM, eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-M8MM8M8 eeeeeee/MeMM, eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]

Meeeeeeee(MM) eeeee eee ee eeeeeeeeeee eeee ee Meeee eeee eeeeeeeee eee eeeee eeeeeee eeeeeeeeeeeeeee. Mee eeeeeeeeeeeeee 88 eeeee eeee eee eeeeeeeeee eeeee eeeeeeeee eeee eeeeeeeeeeeeee-8,8-eeeee (88) eee e-eeeeeee (88) ee eeeeeeee, ee eeee e eeeeeee ee eeeeeeeeeeee 88 eee 88. Meeeeeee eee eeeeeee eeee eeeeeeee ee eeeeeeeeeeee ee eeeeeee eeee eee eeee eee eeeeee ee eee eeeee ee eeeeeeeeeeeeeeee ee eee eeeeeeee. Meeee eee eeeeeee eeeeeee eeeeeeeee, e eeee eeeeeeee eeeeeee eee eeeee eeee eeee eee eeeeeeee(eee)eeeeeeeee(MM) eeeeeeeeeee (MeMMe8•8M8M) ee e eeeee eeeeeee ee eeeeee eeeeeeee eee eeeeeeeeeeeee eeee 8 eeeeeeeeee ee eeeeeeeeeeeeee-8,8-eeeee eee 8 eeeeeeeeee ee e-eeeeeee eeeee ee eeeeeeeeeee 88 ee eee eeeee eeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeee[eeeeeeeeeeeeeeeeeeeeeeeeeeeeeee]eeeeee[‌88‌]

Meeeeeeeeee 8

Me8 Meeeeeeeee Meee Meeee (%) Mee
88 88
Me eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
MeMMe8•8M8M, MeMM, eeeeee 8.8 e 88 88 [‌88‌]
MeMMe8•8M8M, eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
8-MeM8M8 eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
MeMMe8•8M8M, MeMM, eeeeee 8.8 e 88 88 [‌88‌]
MeMMe8•8M8M, eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
8-Mee eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
MeMMe8•8M8M, MeMM, eeeeee 8.8 e 88 88 [‌88‌]
MeMMe8•8M8M, eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
8-MeMM8M8 eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
MeMMe8•8M8M, MeMM, eeeeee 8.8 e 88 88 [‌88‌]
MeMMe8•8M8M, eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
8-MeM8M8 eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]
MeMMe8•8M8M, MeMM, eeeeee 8.8 e 88 88 [‌88‌]
MeMMe8•8M8M, eeee eeee, eeeeeeeee 8.8 eee 88 88 [‌88‌]

Meeeeeeee-eeeeeeee eeeeeeeee ee eeeeeee[eeeeeeeeeeeeeeeeeeeeeeeeee]eeeeeee 88 ee eeeeeeee eee e eee-eee, eeeee-eeeeeeeee eeeeeeee ee eeeeeeeee [88; 8,8-eeeeeeeee-8M-eeeeee-8,8(8M)-eeeee], eeeeeeeee (8), eee eee (M)-8-eeeeeeeee-8-eeeeeeeeeeeee 88 ee eeeeeeeeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeee[eeeeeeeeeeeeeeeeeeeeeeeeee]eeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Meeeeeeeee Meee Meeee (%) Mee
Me eeeeeee/MeMM (8:8), eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-Mee eeeeeee/MeMM (8:8), eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-MeMM8M8 eeeeeee/MeMM (8:8), eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-MeM8M8 eeeeeee/MeMM (8:8), eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-MeM8M8 eeeeeee/MeMM (8:8), eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]
8-M8MM8M8 eeeeeee/MeMM (8:8), eeeeee 8 e 88 [‌88‌]
eeeeeeeeeeeeeee M 88 eeee, eeeeeeeee 88 eee 88 [‌88‌]
eeee, eeeeeeeee 88 eee 88 [‌88‌]

Meeeeeeee eeeeeeeee ee eeeeeeeeeeeeee 88 ee eeeeeeeeeeee eee e eee-eee, eeeee-eeeeeeeee [8 + 8]-eeeeeeeeeeeee eeeeeeee eeeee eeeeeeeeeeeeeee. Mee eeeeeeeeee eeeee eeeeeeeee eeee eeeeeeeee (88) eee e-eeeeeee (88) ee eeeeeee ee eee eeeeeeeeeeeeee 88 ee eeeeee eeeeeee[eeeeeeeeeeeeeeeeeeeeeeeeeee]eeeeeee 88 ee eeee eeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeee[eeeeeeeeeeeeeeeeeeeeeeeeeee]eeeeeee[‌88‌]

Meeeeeeeeee 88

Me8 Meeeeeeeee Meee (e) Meeee (%) Mee
Me MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-MeM8M8 MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-Mee MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-MeMM8M8 MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
8-MeM8M8 MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]
MeMM 8.8 88 [‌88‌]
MeMM, eeeeee eee 8.8 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8′-(8M-Meeeee-8-eeeeeeee)-8′-eeeeee-8-eee-8′-eeeeeeeeeee[eeeeeeee-8,8′-eeeeeeeeeee]-8′-eeeeeeeeeeeee 8; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeeeee eeeeee 8 (8.8 eeee), eeeeeeeee (8; 8.8 eeee), eee 8-(8M-eeeeee-8-eeeeeeee)-8-eeeeeeeeeeeeeeeeeee (8; 8.8 eeee) ee MeMM (88 eM) eee eeeeeeee eee 88 eee eee eeee eeeeeee ee eeee ee ee. Mee eeeee eeeeee eee eeeeeeeee ee eeeeeeeeee, eeeee, eee eeeeeeeeeeeeee (MeMM) ee eeeeee eee eeee eeeeeee 8.

8e-Meeeee-8-eeeeee-8,8e-eeeeeee-8M-eeeee[[8]eeeeeeeeeee[8,8-e]eeeeeee-8,8′-eeeeeeee]-8′,8(8eM)-eeeee (8, M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeee (8; 8.88 e, 8.8 eeee), 8-eeeeee-8M-8-eeeeeeeeee-8-eee (8, M8 = M8 = M; 8.88 e, 8.8 eeee), eee eeeeee (8, M8 = M; 8.88 e, 8.8 eeee) eee eeeeee ee eeeeee ee eeeee eeeeeee (88 eM) eeeeeeeeee 8-Å eeeeeeeee eeeeee (8.8 e) eeee eeeeeeee eee 88 e. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeee ee MMM eee, eeeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeee eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeee (MeMM) ee eeeeee eeeeeeeeeee 8 (M8 = M8 = M8 = M); eeeee: 88%.

8-Meeeee-8,8e-eeeeeee-8M-eeeee[[8]eeeeeeeeeee[8,8-e]eeeeeee-8,8′-eeeeeeee]-8′,8(8eM)-eeeee (88, M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeee (8; 8.88 e, 8.8 eeee), 8-eeeeee-8M-8-eeeeeeeeee-8-eee (8, M8 = M8 = M; 8.88 e, 8.8 eeee), eee eeeeee (8, M8 = M; 8.88 e, 8.8 eeee) eee eeeeee ee eeeeee ee MeMM (88 eM) eeeeeeeeee 8-Å eeeeeeeee eeeeee (8.8 e) eeee eeeeeeee eee 88 e. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeee eee eee eeeee eeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeeeeeeeeeee (MeMM) ee eeeeee eee eeeeeeeeeee 88 (M8 = M8 = M8 = M); eeeee: 88%.

8′-Meee-8-eee-8′,8′,8′,8e′-eeeeeeeeeeeeeee[eeeeeeee-8,8′-eeeeeeeeeee]-8′,8′(8′M)-eeeeeeeeeeeeeee 88 eee 8′-Meee-8-eee-8′,8′,8′,8e′-eeeeeeeeeeeeeee[eeeeeeee-8,8′-eeeeeeeeeee]-8′,8′(8′M)-eeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee e-eeeeeee (88; 8.8 eeee), eeeeeeeeeee eeeeeeeeeeee 88 (8.8 eeee), eee eeeeeeeeeeeee 88 (8.8 eeee) ee eeeee eeeeeee (88 eM) eeeeeeeeee 8-Å eeeeeeeee eeeeee (888 ee) eee eeeeee ee eeeeee eeee eeeeeeee. Mee eeeeeee eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8) ee eeee eee eeeeeeee 88 eee 88.

8′-Meeeeeeeeeeee[eeeeeeeeeee-8,8′-eeeeeeeeeee-8′,8′′-eeeeeeee]-8,8′′-eeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee 8-eeeeeeeeeeeeeeeeeeeeee 88 (8.8 eeee), eeeeee (8; 8.8 eeee), eee eeeeeeeee (8; 8.8 eeee) eee eeeeeeee ee MeMM ee 8,8-eeeeeee eeeee eee eeeeeeee eeeeeeeee eee eeeeeeeeeee, ee eeeeeeeee ee MMM. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 88:8) ee eeee eee eeeeeee-eeeee eeeeeeeeeee 88.

8′,8′,8′,8′,8′,8e′-Meeeeeeeeeeeeeee[eeeeeeee-8,8′-eeeeeeeeeee-8′,8′′-eeeeeeee]-8,8′′-eeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeeeeee, Meeeee Mee, eee Meeeeeeeee:[‌88‌]

M eeeeeee ee eeeeee (8; 8 eeee), e-eeeeeee (88; 8 eeee), eee eeeeeeeeeeeee 88 (8 eeee) eee eeeeeee ee MeMM (88 eM) eeeeeeeeee eeeeee eee (888–888 eeee; 888 ee). Mee eeeeeee eee eeeeeeeee ee eeeeeeeeee eeeee eee eeeeeeee eee eeeeeeee, ee eeeeeeeee ee MMM. Mee eeeeeee eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8). Mee eeeeeeee 88 eeee eeeeeeeeeeeeee (MeMM).

8′-Meeeeeeeeeeee[eeeeeeeeeeeeee-8,8′-eeeeeeeeeee-8,8′′-eeeeeeeee]-8,8′′-eeeeee 88; Meeeeee Meeeeeeee eeeee Meeeee Meeeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeee (8; 8 eeee), eeeeeeeeeeeeee-8,8-eeeee (88; 8 eeee), eee (M)-8-eeeeeeeee-8-eeeeeeeeeeee 88 eee eeeeeeee ee eeeeeee/MeMM (8:8). Meeeeeeeee ee eee eeeeeeee eee eeeeeeeee ee MMM eeeeeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8).

8′-Meeeeeeeeeeee[eeeeeeeeeeeeee-8,8′-eeeeeeeeeee-8,8′′-eeeeeeeee]-8,8′′-eeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeeeeeeeee M 88 Meee eee Meeeeeeee Meeeeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeee (8; 8 eeee), eeeeeeeeeeeeee-8,8-eeeee (88; 8 eeee), eee (M)-8-eeeeeeeee-8-eeeeeeeeeeee 88 (8 eeee) eee eeeeee eeee eeeeeeeeeeeeeee M 88 eeee eee eeeeeeeeee eeeee eeeeeeeee eeeeeeeeee (888 M). Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeeee eeee MM8Me8 eee eee eeeeeee eeeee eee eeeee (MeMM8). Mee eeeeeee eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8).

8′-Meeeeeeeeeeee[eeeeeeeeeeeeee-8,8′-eeeeeeeeeee-8,8′′-eeeeeeeee]-8,8′′-eeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeee Meeeeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeee (8; 8 eeee), eeeeeeeeeeeeee-8,8-eeeee (88; 8 eeee), eee (M)-8-eeeeeeeee-8-eeeeeeeeeeee 88 (8 eeee) eee eeeeee eee eeeeeeeeee eeeee eeeeeeeee eeeeeeeeee (888 M). Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeee ee eeeee ee ee eeeee ee eeeeeeeeee, eee eee eeeee eeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8).

8′,8′,8′,8′,8′,8e′-Meeeeeeeeeeeeeee[eeeeee-8,8′-eeeeeeeeeee-8′,8′′-eeeeeeee]-8,8,8′′-eeeeeee 88; Meeeeee Meeeeeeee Meeee Meeeeeeeeeee, Meeeee Mee, eee Meeeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeee (88; 8 eeee), e-eeeeeee (88; 8 eeee), eee eeeeeeeeeeeee 88 (8 eeee) eee eeeeeee ee MeMM (88 eM) eeeeeeeeee eeeeee eee (888–888 eeee; 888 ee). Mee eeeeeee eee eeee eeeeeeeee ee eeeeeeeeee eeeee eee eeeeeeee eee eeeeeeee, ee eeeeeeeee ee MMM. Mee eeeeeee eee eeee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8). Mee eeeeeee eee eeeeeeeeeeeeee (MeMM).

References


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