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Biosynthetic studies of marine lipids. 24. Experimental demonstration of an unprecedented cyclopropane .fwdarw. cyclopropane rearrangement in the biosynthesis of the sponge sterol petrosterol

✍ Scribed by Doss, George A.; Proudfoot, John R.; Silva, Christopher J.; Djerassi, Carl

Book ID
127374577
Publisher
American Chemical Society
Year
1990
Tongue
English
Weight
895 KB
Volume
112
Category
Article
ISSN
0002-7863

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Biosynthetic studies of marine lipids. 6
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Petrosterol, an unusual cyclopropane-containing marine sponge sterol, is shown, unexpectedly, to be derived by SAM biomethylation of 24-methylenaoholesterol via a complex rearrangement process.

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In vivo isomerization of cyclopropenes has been demonstrated for the first time through feeding experiments of appropriately labeled cyclopropene sterols (lc-4c) in the sponge Calyx nicaeensis.