Ionic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations
| Title | Ionic hydrogenation-directed stereoselective construction of C-20(H) stereogenic center in steroid side chains: Scope and limitations |
| Publication Type | Journal Article |
| Year of Publication | 2017 |
| Authors | Shingate, BB, Hazra, BG |
| Journal | Tetrahedron |
| Volume | 73 |
| Issue | 17 |
| Pagination | 2396-2414 |
| Date Published | APR |
| Type of Article | Article |
| 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 |
| DOI | 10.1016/j.tet.2017.03.029 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.377 |
Divison category:
Organic Chemistry