A novel synthetic approach to (20R)- and (20S)-21-hydroxy steroids. Synthesis of a marine sterol 21-hydroxycholesterol.

Abstract:

:A short and efficient synthesis of steroid synthons, di(tert-butyldimethylsilyl) ethers of 3,21-dihydroxy-24-nor-chol-5-en-23-al (8 and 10) and of ethyl 3,21-dihydroxy-25-homo-chola-5,23-dien-25-oate (9 and 11), having natural (20R) and unnatural (20S) configuration from 3β-(tert-butyldimethylsilyloxy)-14α,20ξ-card-5-enolide (2) is reported. Further elongation of the side chain of these synthons provides a new method for the synthesis of (20R) and (20S)-21-hydroxy steroids. The utility of the method was exemplified by the synthesis of a natural marine sterol - 21-hydroxycholesterol (18).

journal_name

Steroids

journal_title

Steroids

authors

Koenig H,Skiera I,Błaszczyk K,Paryzek Z

doi

10.1016/j.steroids.2011.01.010

subject

Has Abstract

pub_date

2011-04-01 00:00:00

pages

517-23

issue

5

eissn

0039-128X

issn

1878-5867

pii

S0039-128X(11)00039-0

journal_volume

76

pub_type

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