Synthesis of Azadirachtin: A Long but Successful Journey

Synthesis of Azadirachtin: A Long but Successful Journey

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...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2007-01, Vol.46 (40), p.7629-7632
Hauptverfasser: Veitch, Gemma E, Beckmann, Edith, Burke, Brenda J, Boyer, Alistair, Maslen, Sarah L, Ley, Steven V
Format: Artikel
Sprache:eng
Schlagworte:
azadirachtin
Claisen rearrangement
epoxidation
Limonins - chemical synthesis
Limonins - chemistry
Mesylates - chemistry
Molecular Structure
radical cyclization
total synthesis
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Zusammenfassung: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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200703027