Biosynthesis of the nicandrenoids: stages in the oxidative elaboration of the side chain and the fate of the diastereotopic 25-methyl groups of 24-methylenecholesterol
- 1 January 1986
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 18,p. 1459-1460
- https://doi.org/10.1039/c39860001459
Abstract
Experiments with Nicandra physaloides plants show that the insect antifeedant steroid Nic-1 (1) is formed from 24-methylenecholesterol: in double bond isomerisation to 24-methylcholesta-5,24-dien-3β-ol, the 25-(pro-S) methyl in (2) becomes the 25-(pro-Z) methyl, in (3); further oxidations lead to triol (6) and hence to lactol (1) with partial retention of 26-hydrogen.Keywords
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