Chiral acyl anion equivalents: asymmetric synthesis of 11-deoxy-ent-prostaglandin intermediates
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 4,p. 1284-1286
- https://doi.org/10.1039/p19810001284
Abstract
Conjugate addition of the chiral formyl anion equivalent p-tolyl p-tolylthiomethyl sulphoxide (+)-(S)-(1) to the cyclopentenone derivative (2a) leads to the adduct (3a) in 45% yield with high diastereoselectivity. Reduction of (3a) gives the dithioacetal (4a), an interesting optically pure intermediate in the synthesis of 11-deoxy-ent-prostanoids. The high selectivity, contrasting with a lower selectivity observed using cyclopentenone, is to be ascribed to more severe steric demands in the transition state.This publication has 2 references indexed in Scilit:
- Synthesis of new allenic prostanoidsTetrahedron, 1979
- Prostaglandins. Part 4. Synthesis of (±)-11-deoxyprostaglandins from 2-(ω-hydroxyheptyl)cyclopent-2-enonesJournal of the Chemical Society, Perkin Transactions 1, 1976