Organocuprate conjugate-addition–enolate-alkylation reactions: a new synthesis of 11-deoxyprostaglandins
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1407-1410
- https://doi.org/10.1039/p19810001407
Abstract
A short synthesis of a key 11-deoxyprostaglandin precursor, 6β-[(E)-3-oxo-oct-1-enyl]-cis-α-2-oxabicyclo-[3.3.0]octan-3-one (11), is reported. Important reactions in the synthesis include preparation of 2α-allyl-3β-{(E)-3-[dimethyl-(t-butyl)silyloxy]oct-1-enyl}cyclopentanone (4) by an organocuprate conjugate-addition–enolate-alkylation reaction, regiospecific epoxidation–cyclisation of the alcohol (7) to give 6β-{(E)-3-[dimethyl-(t-butyl)silyloxy]oct-1-enyl}-3-hydroxymethyl-cis-α-2-oxabicyclo[3.3.0]octane (9), and oxidative degradation of (9) with manganese dioxide to give 6β-{(E)-3-[dimethyl-(t-butyl)silyloxy]oct-1-enyl}-cis-α-2-oxabicyclo-[3.3.0]octan-3-one (10).This publication has 3 references indexed in Scilit:
- Short, simple, stereocontrolled, steroid synthesis: (.+-.)-11-oxoequilenin methyl ether and a new 9,11-seco-13-ethyl steroidThe Journal of Organic Chemistry, 1979
- Synthesis of the four isomers of 5-hydroxy-PGI1Prostaglandins, 1978
- Prostaglandin chemistry—VIIITetrahedron, 1977