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Biogenetic-type syntheses of obtusastyrene and 4-methoxydalbergione

✍ Scribed by L. Jurd

Publisher: Elsevier Science
Year: 1969
Tongue: French
Weight: 160 KB
Volume: 10
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)88293-9

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✦ Synopsis

Some years ago Ollis and his associates noted that cinnamylphenols co-occur with dalbergiones and other neoflavanoids in Dalbergia and Machaerium species, and suggested that the biogenesis of both of these new types of natural products may involve C-cinnamylation of phenols, e.g. by cinnamyl pyrophosphate (1, 2, 3). Mechanistic support for this the&y was recently provided (4, 5) by the observation that cinnamyl alcohol condensed readily with pyrogallol or resorcinol in aqueous acetic acids to yield cinnamylphenols and isomeric neoflavanoids.

Cardillo, Cricchio and Merlini ( ) have since prepared a number of model cinnamylphenols by this method and have shown, furthermore, that these compounds are readily oxidized by quinones to flav-3-enes, which then disproportionate to flavans and flavylium

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