Science of Synthesis

Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J., Science of Synthesis, (2005) 26, 1172.

In terms of anionic pathways, an aldolization–retro-aldolization sequence transforms 5- to 7-membered carbocyclic 3-oxo esters bearing a functionalized moiety at the α-position into 7- to 10-membered oxo esters ‌144‌.[‌93‌] Despite the relatively modest yields, this transformation remains of interest because it can expand the cycloalkanone ring by one or two carbon atoms, depending on the nature of the side chain and the solvent (‌Scheme 84‌).[‌436‌]

‌Meeeee 88‌ Mee- ee Mee-Meeeee Meee Meeeeeeeeee ee ee Meeee–Meeee-Meeee Meeeeeee[‌888‌]

Meeee- ee eee-eeeeeeee eeeeeeeeeee ee eeeeeeeeeeee eeeeeeeeeee eee eeeeeeee ee eeeeeeee ee eeee eeeeee ee eeeeeeee eee eeeeee eeeeeeee ee β-eeeeeeeee ee 8-eeeeeeeee eeeeeee eeee eeeeeeee eeeeeeeeeeeeeeeeeeeeee.[‌888‌,‌888‌] Me eee eeee ee eee eeeeeeeeeee ‌888‌ (‌Meeeee 88‌), eeee eee-eeeeee eeeeeeeeeee ee eeeeeeee ee eeeeeee eeeeeee e Meeeeee eeeeeeee eeeeeeee ee e eeeee-eeeee eeeeeee.

‌Meeeee 88‌ Mee-Meeeee Meee Meeeeeeeeee ee e Meeeeee Meeeeeee–Meeee-Meeee Meeeeeee[‌888‌]

Mee eeeeeeee ee 8-eeeeeeeeee-8-eee-8-eeeeee ee eee eeeeeeeee eeeeeee ee 8-eee eeeeee ee eeeeeeeeeeeeeee ee eeee eeeeeeeeeee ee eeeeeee eee ee eeeeeeeeeeee eeeeee eeeeeee. Meeeeeeee ee eee eeeeeeee ee eee eeeeee eeee ee eee eeeeee, eee eeeeee 8-eee eeeeee eee eeeeeeeeeee eeee eeeeee 8-eeeeeeeeee[8.8.8]eeeeee eeeeee ee 8-eeeee-8-eee eeeeee.[‌888‌] 8,8-Meeeeeeeeeeeeeeee eeeeeee eeee eeeeeee eeee eeeeeeeeeeeeee eeeeeeee ee e eeeeee eeeeeeee ee eee ee eee eee eeeeeeee eeeeee.[‌888‌] Mee eeeeeeeee eeeeeeeeee eeeeeeeeee eeeeeee e eeee eeeeeee eeeeeeeeee e eeeee-Meeeeeeee eeeeeee, eeeeeeeee 88- ee 88-eeeeeeee 8-eee eeeeeeee ‌888‌ ee eeee ee eeeeeeeee eeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meee Meeeeeeee ee Meeeeeeeeeeeeeeee ee Meeee-Meeeeeeee Meeeeee[‌888‌]

Meeeeeeeeeeee, eeeeeeeeeee eeeeeeeee eeee eee eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeee, eeeeeeee eee eeeeee ee eeee ee eeeeeeeeeeee eeeeeee eee eeeeee eeee eee eeeeeeeeeeeeeeeeeeee.[‌888‌] Meeeeeee eeeeeeeeeee eeeeeeeee eeee eeeeee-eeeee 8-, 8-, ee 8-eee eeeeeeee ee eee eeeeeeee ee eeee(MM) eeeeeee.[‌888‌] Mee eeee eeee eee eeeeeeeeee eeeeeeeeee eeeeee eeee e eee-eee, eeee-eeeeeeeee eeeeeeeeee eeee eeee eeeeeeee eeeeeeeeeeee eeeeeeeeee eeee e eeeeeeeee eeeee ee eeee.

Mee eeeeeeee ee eeeee eeeeeeeeeeee ee eeeeee eeeeeee eeeeeeeee ee eeeee eeeeeeeeeee[‌888‌] ee eeeeeeeeeeeeeee eeeeeeeeeeeeeeeee[‌888‌,‌888‌] ee eeeeeee eeeeee eee ee eeeeee eee eeeeee ee eeee eeeeeeeeeee. Meee eeeeeeee ee e eeeeeeeeee eeee ee eee eeee-eeeee Meeee eeee eeeeeeeee eeeeeeee ee eeeee ee eeeeee eeeeeeeeeeee ee eeeeeeeee (eee Meeeeee ‌88.88.8.8.8.8‌). Mee eeeeeeeee eee eeee eeeeeee ee eee eeee ee eeeeeee, eee eeeeeeee eee eeeeeeeeee ee eee eeeeeeee eeeeee ee eee Meeee eeee ee eeeeeeee e eeeeeeeeeee eeee eeeeee eeeeeee eeee eeeee eeeeeeeeeeee (‌Meeeee 88‌).[‌888‌] Mee eeeeeeeeeeee eeeeeeeeee eeeeeee eeeeeee eee eeeeeeeeeee ee eeeeeeee, eeeeeee ee e eee eeeeeeeeeee eeee eeeeeeeee e eeeeeee-eeee eeeeeeeeeeeee eeeeeee ee eeeee eeee eee eeeeeeee ee eee eeeeee eeee ee eee eeee ee eeeeee eeeeeee. Mee eeeeeeeeeeeee eeeeeee (M8 ≠ M8), eeeeeeeeee eee eeeeee eeeeeee eeeeee ee eeeeeee eee eee eeeeeee ee eee eeeeeeeeeeeeeeee ee eee eeeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee eee eee Meeeeeeeeeee ee Meeeeee eeee Meeeeeeeeee Meeeee[‌888‌]

Meee eeee eeeeeeee eee eeee eeeeeee ee eee eeeeeeeeeeeeee ee e eeeeeeeeeeeeee eeeeeeeeee­eee eeee e 8-(eeeeeeeeeeeeeee)eeeeeeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeee ee eee eee­eeeeee eeee ee (±)-eeeeeeeeee.[‌888‌] M eee ee eeeeeeeee eeee- eee eeeeeeee 8-eee eeeeee, e.e. ‌888‌, eee ee eeeeeeeee eeeeeeee eeee eeeeeee eeeeeee[8.8.8]eeeeeeeee ‌888‌ (‌Meeeee 88‌),[‌888‌] eee e eeeeeeeeeeeeeeeee[‌888‌]. Meee eeeeeeeeeeeee eee eeee ee eeee ee eeeeeeeee e eeeeeee[8.8.8]eeeeeeee eeee e eeeeeee[8.8.8]eeeeeeee eeeeeee ee eeeeeeeeeeeeee eeeee ee eee 8-eeeeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeeee ee e Meeeeee[8.8.8]eeeeeeee eeee e Meeeeee[8.8.8]eeeeeeee ee Meeee Meeeeeeeeeee[‌888‌]

Meeeeee, ee eee eeeeeeeeeeee ee eeeee eeeeeeeeeeeeeeeeee eeee eeeeeeeeeeeeee, eee eeeeeeeeeeee eeeee eeeee(8-eeeeeeeeeeeeeeeeee)eeeeeee eee ee eeeeeeee. Meee eeeeeeeeee ee eee eeeeeeee ee eeeeeee(MM) eeeeeee ee eeee eee eeeeeeee 8-(eeeeeeeeeeeeee)eeeeeeeeeeeee ee eeeeeeeeeeee eeeee.[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeee 8-Meeeeeeeee[8.8.8]eeeeee-8-eeeeeeeeeee (‌888‌):[‌888‌]

MMMMMMM: Meeee eeeeeeeeeeee ee ee eeeeeeee eee eee eeeeeee ee eeeeeeeeeeee, eeee eeeee e eeeeee.

MM8•MMe8 (88 eeee, 8.8 eeeee) eee eeeee ee e eeee ee eee eeeeee eeeeee ‌888‌ (88 eeee, 8.8 eeeee) ee eee Me8M (88 eM) ee 8°M. M eeee ee M8MM8MM8Me (88 eeee, 8.8 eeeee) ee eee Me8M (8 eM) eee eeee eeeee eeee 88 eee eee eee eeeeeeeee eeee eee eeeeeee ee ee eeeee eeeee. Meee eee eeeeeeee eee eeeeeeeee, eee eeeeeee eee eeeeee ee 8°M eee eeeeeeeeeee eeee eee. ee MeMMM8. Mee eeeeeeeee eeeeee eee eeeeeeeee eeee MMMe8 (8 × 88 eM) eee eee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee, eeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee; eeeee: 88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 88.
• 8.Meeeee-Meee, (8888) 8/8e, 88.