Ring-D aromatic phytosteroids; a model for biogenesis by way of carbon radical rearrangement

SP Green, DA Whiting

文献索引：Green, Stuart P.; Whiting, Donald A. Journal of the Chemical Society - Perkin Transactions 1, 1996 , # 10 p. 1027 - 1034

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摘要

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 ...