An efficient one-pot synthesis of 5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione from 9-bromide-11-hydroxypregna-1, 4, 16-trien-3, 20-dione by two annulation reactions

Ping Jia; Xuling Wu; Yongping Yu; Guolin Zhang

doi:10.1016/j.steroids.2008.10.018

An efficient one-pot synthesis of 5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione from 9-bromide-11-hydroxypregna-1, 4, 16-trien-3, 20-dione by two annulation reactions

Steroids. 2009 Feb;74(2):229-32. doi: 10.1016/j.steroids.2008.10.018. Epub 2008 Nov 11.

Authors

Ping Jia¹, Xuling Wu, Yongping Yu, Guolin Zhang

Affiliation

¹ Department of Medicinal Chemistry, College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, PR China.

PMID: 19041660
DOI: 10.1016/j.steroids.2008.10.018

Abstract

An efficient method to prepare 5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione in one pot was reported. Treatment of 9-bromide-11-hydroxypregna-1, 4, 16-trien-3, 20-dione with Raney Ni in absolute ethanol afforded 5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione by two annulation reactions in reasonable yield. The absolute configuration was also confirmed by X-ray crystal analysis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Crystallography, X-Ray
Halogenation
Pregnatrienes / chemistry*
Pregnenediones / chemistry*
Pregnenes / chemical synthesis*
Pregnenes / chemistry
Stereoisomerism
Substrate Specificity

Substances

5, 9-cyclo-1, 11-oxido-pregn-16-ene-3, 20-dione
9-bromide-11-hydroxypregna-1, 4, 16-trien-3, 20-dione
Pregnatrienes
Pregnenediones
Pregnenes