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A Novel Approach to Combretastatins: From trans ‐Epoxide to CA‐4 and Its Dioxolane Derivative
Author(s) -
Lupattelli Paolo,
D'Auria Maurizio,
Di Blasio Nadia,
Lenti Francesca
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800957
Subject(s) - chemistry , epoxide , dioxolane , derivative (finance) , deoxygenation , ylide , acetone , yield (engineering) , stereoselectivity , stereochemistry , organic chemistry , catalysis , materials science , financial economics , economics , metallurgy
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 Weinheim, Germany, 2009)