o-Quinone methide based approach to isoflavans: application to the total syntheses of equol, 3′-hydroxyequol and vestitol

✍ Scribed by Santosh J. Gharpure; A.M. Sathiyanarayanan; Prasad Jonnalagadda

• Book ID: 104095177
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 141 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.03.003

✦ Synopsis

A concise strategy is developed for the synthesis of isoflavans employing a Diels-Alder reaction between o-quinone methides and aryl-substituted enol ethers followed by reductive cleavage of the acetal group. The method is extended towards the total syntheses of equol, 3 0 -hydroxyequol and vestitol.