(1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol → (1s,3r)-1-Hydroxy-3-(ethyl-carboxymethoxy)-4-cyclopentene

Participants

Reaction Steps

Compound 14 was subjected to general procedure D. Yield=77%. TLC: Rf=0.29 (10% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 1.25 (t, 3H), 1.60 (m, 1H), 2.65 (m, 1H), 4.10 (s, 2H), 4.20 (q, 2H), 4.55 (m, 1H), 4.65 (m, 1H), 5.95 (m, 2H). Subsequent subjection of the product to general procedure I gave compound 15. Yield=79%. TLC: Rf=0.65 (EtOAc). 1H NMR (400 MHz, CDCl3): δ1.25 (t, 3H), 1.65 (m, 1H), 1.75 (s, 1H), 2.65 (m, 1H), 4.10 (s, 2H), 4.20 (q, 2H), 4.45 (m, 1H), 4.65 (m, 1H), 6.05 (m, 2H).

Provenance & Evidence