Ionic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations

TitleIonic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations
Publication TypeJournal Article
Year of Publication2017
AuthorsShingate, BB, Hazra, BG
JournalTetrahedron
Volume73
Issue17
Pagination2396-2414
Date PublishedAPR
Type of ArticleArticle
Abstract

Stereoselective synthesis of steroidal C-20 tertiary alcohols with n-butyl, vinyl, furyl, thienyl, thiazolyl, aryl and pyridyl side chains via Grignard reaction or organolithium reagents have been realized starting from readily available 16-dehydropregnenolone acetate. The ionic hydrogenation of steroidal C-20 tertiary alcohols having furyl, methylfuryl, thienyl, phenyl and 4-methoxyphenyl side chains, resulted into the deoxygenated product with C-20 natural configuration in excellent yields. However, the alkyl, thiazolyl and pyridyl incorporated steroidal C-20 tertiary alcohols were failed under the same reaction condition. The scope of ionic hydrogenation is further highlighted through the stereoselective reduction of steroidal C-20,21-ene compounds with furyl, thienyl and 4-methoxyphenyl side chains gave the saturated compounds with C-20 natural configuration

DOI10.1016/j.tet.2017.03.029
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.377

Divison category: 
Organic Chemistry