A Novel Approach to Combretastatins: From  trans ‐Epoxide to CA‐4 and Its Dioxolane Derivative | Zendy

Lupattelli Paolo | Zendy; D'Auria Maurizio | Zendy; Di Blasio Nadia | Zendy; Lenti Francesca | Zendy

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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)

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