Studies of the synthesis of biomarkers. VII. Synthesis of 5 alpha-(17R,20R)-14,15-secocholestane.

Abstract:

:5 alpha-(17R,20R)-14,15-Secocholestane (12) was synthesized from cholesterol (1) in 12 steps. The key intermediate, 5 alpha-cholest-14-en-3 beta-yl acetate (4), underwent ozonization, reduction, hydrolysis, and oxidation to provide 5 alpha-14,15-secocholesta-3,14,15-trione (8). One of the Clemmensen reduction products of 8 is 5 alpha(17R,20R)-14,15-secocholest-15-ol (11); treatment of the alcohol (11) with tosyl chloride and subsequent reduction with lithium aluminum hydride yielded the target molecule (12).

journal_name

Steroids

journal_title

Steroids

authors

Li TS,Li YL,Liang XT

doi

10.1016/0039-128x(90)90042-a

subject

Has Abstract

pub_date

1990-06-01 00:00:00

pages

263-5

issue

6

eissn

0039-128X

issn

1878-5867

pii

0039-128X(90)90042-A

journal_volume

55

pub_type

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