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Rhodium(I)-catalyzed addition of phenols to dienes. A new convergent synthesis of vitamin E

✍ Scribed by Hugues Bienaymé; Jean-Erick Ancel *; Pierre Meilland; Jean-Pierre Simonato

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 145 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00381-6

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✦ Synopsis

A highly convergent and atom-economical synthesis of (dl)-[α]-tocopherol (vitamin E) is proposed, the realization of which was made possible by the discovery of the regioselective Rh(I)-catalyzed arylation of β-springene with trimethylhydroquinone. Other phenolic compounds and 2-substituted-1,3-dienes were shown to undergo this transformation.

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