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Synthesis of bicyclo[3.2.1]octanes by a tandem Diels-Alder-carbocation cyclization strategy

✍ Scribed by James H. Rigby; Atul S. Kotnis

Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 213 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)96665-6

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✦ Synopsis

The bicyclo[3.2.l]octane ring system is assembled by a three-step process featuring a thermally induced [4+2] cycloaddition followed by a 1,3benzodithiolium ion mediated cyclization onto an enol or silyl enol ether double bond.

The bicyclo[3.2.l]octane carbon skeleton is a common structural subunit in a number of important natural products1 and many methods have been developed to construct this ring system.2 In connection with our studies

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