Synthesis of dehydro-oogoniol, a female-activating hormone of Achlya: the progesterone route.

Abstract:

:The structure of dehydro-oogoniol (3 beta,11 alpha,15 beta,29-tetrahydroxystigmasta-5,24(28)(E)-dien-7-one), a female-activating hormone of the water mold Achlya, has been confirmed by synthesis. The starting material was progesterone, which was converted to the 11 alpha, 15 beta-dihydroxy derivative by microbiological hydroxylation with Aspergillus giganteus (ATCC 10059). The side chain was constructed in a stepwise manner by means of Wittig and Horner-Emmons reactions, and the C-7 ketone was then introduced by allylic oxidation. The biological activity of the synthetic compound was the same as that of the natural hormone.

journal_name

Steroids

journal_title

Steroids

authors

McMorris TC,Le PH,Preus MW,Schow SR,Weihe GR

doi

10.1016/0039-128x(89)90019-6

subject

Has Abstract

pub_date

1989-03-01 00:00:00

pages

345-61

issue

3-5

eissn

0039-128X

issn

1878-5867

pii

0039-128X(89)90019-6

journal_volume

53

pub_type

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