Synthesis of dehydro-oogoniol, a female-activating hormone of Achlya: the progesterone route.
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.
McMorris
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TC
Department of Chemistry, University of California, San Diego, La Jolla 92093.
Le
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Preus
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Schow
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SR
Weihe
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D000818:Animals; D001230:Aspergillus / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D008411:Chytridiomycota / Q000378:metabolism*; D005260:Female; D009868:Oomycetes / Q000378:metabolism*; D010840:Phytosterols / Q000138:chemical synthesis*; D011374:Progesterone / Q000378:metabolism; D013265:Stigmasterol / Q000031:analogs & derivatives / Q000138:chemical synthesis*
D010840:Phytosterols; D011374:Progesterone; C061537:dehydroogoniol; D013265:Stigmasterol