Ring-D aromatic phytosteroids; a model for biogenesis by way of carbon radical rearrangement
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 1027-1034
- https://doi.org/10.1039/p19960001027
Abstract
A mechanism is postulated for the biogenesis of the unique ring-D aromatic phytosteroids from Nicandra physaloides, which involves rearrangement, ring expansion, and aromatisation of a carbon radical generated by cytochrome P450 (Scheme 1). In support, model hydrindene acids 15b and 18b have been synthesized and subjected to homolytic decarboxylation; the latter acid yielded 6-methyltetralin 24, in biomimetic fashion. The isomeric acid afforded not only 6-methyltetralin 24 but also 5-methyltetralin 26; mechanisms for this unusual rearrangement are discussed.Keywords
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