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Intramolecular ene reaction on a bicyclo[3.2.1]octane system: an alternative route to (−)-kainic acid

✍ Scribed by Hideaki Hirasawa; Takahiko Taniguchi; Kunio Ogasawara

Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 72 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01558-1

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✦ Synopsis

The intramolecular ene reaction of the 1,6-diene on a bicyclo[3.2.1]octane framework proceeds in a highly diastereoselective manner to form a trisubstituted pyrrolidine on the pyran ring in excellent yield. Its stereochemistry has been determined unambiguously by converting it into the known compound serving as a key intermediate of (-)-kainic acid.

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