(Chemical Equation Presented) 22 Years in the making: Azadirachtin (1) was synthesized for the first time by a highly convergent approach, utilizing a Claisen rearrangement and a radical cyclization as key steps. End-game strategies relied on intermediate 2, which could be obtained by synthetic methods as well as by degradation of 1. Bn = benzyl, TBS = tert- butyldimethylsilyl.
Veitch, Gemma E.,Beckmann, Edith,Burke, Brenda J.,Boyer, Alistair,Ayats, Carles,Ley, Steven V.
Chemistry of Insect Antifeedants from Azadirachta Indica (Part 19): A Potential Relay Route for the Synthesis of Azadirachtin.
A potential relay route for the synthesis of azadirachtin (1) has been established.An advanced intermediate 4 has been prepared and methods to convert this back to the natural product has been developed, in particular, the reintroduction of the enol double bond using an acetal exchange process.
Denholm, Alastair A.,Jennens, Lyn,Ley, Steven V.,Wood, Anthony
p. 6591 - 6604
(2007/10/02)
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