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

Participants

Reaction Steps

Compound 22 was subjected to general procedure D. Yield=71%. TLC: Rf=0.33 (10% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 1.30 (t, 3H), 1.90 (m, 1H), 2.20 (m, 1H), 4.05 (s, 2H), 4.20 (q, 2H), 4.75 (m, 1H), 5.05 (m, 1H), 6.00 (m, 2H). Subsequent subjection of the product to general procedure K gave compound 23. Yield=91%. TLC: Rf=0.25 (50% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ1.25 (t, 3H), 2.00 (m, 1H), 2.25 (m, 1H), 4.05 (s, 2H), 4.20 (q, 2H), 4.80 (m, 1H), 5.05 (m, 1H), 6.05 (m, 2H).

Provenance & Evidence