A Novel Approach to Combretastatins: From trans??Epoxide to CA??4 and Its Dioxolane Derivative

P Lupattelli, M D'Auria, N Di Blasio…

Index: Lupattelli, Paolo; D'Auria, Maurizio; Di Blasio, Nadia; Lenti, Francesca European Journal of Organic Chemistry, 2009 ,  # 1  p. 141 - 145

Full Text: HTML

Citation Number: 3

Abstract

Abstract The trans-epoxide derivative of Combretastatin A-4 wasstereoselectively prepared in good yield by sulfur ylide mediated epoxidation of silyl-protected isovanillin. From this key intermediate, a formal synthesis of CA-4, by stereoselective deoxygenation and photoisomerization, was achieved. Alternatively, a trans-dioxolane derivative was obtained bystereoselective acetone insertion.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 ...