Radical cyclization strategies to terpenoids; syntheses of (±)-β-cuparenone, (±)-laurene and epilaurenes
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AbstractRadical cyclization of the bromide 8, obtained in 5 steps from the ketone 9, furnished exclusively 14via 6-endo trig cyclization with out any observable amount of 5-exo trig product 1. 5-Exo dig radical cyclizatlon of the bromo acetate 23, prepared from 18via the aldehyde 21, followed by routine transformations furnished the cyclopentenone 26, an immediate precursor to β-cuparenone (2). Similarly, total synthesis of laurenes 4 and 5 was achieved via the 5-exo dig radical cyclization of the xanthate 28, obtained from the aldehyde 21.

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