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Synfacts 2008(2): 0111-0111
DOI: 10.1055/s-2007-992496
DOI: 10.1055/s-2007-992496
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Relay Synthesis of Azadirachtin
Rezensent(en):Philip KocienskiG. E. Veitch, E. Beckmann, B. J. Burke, A. Boyer, S. L. Maslen, S. V. Ley*
University of Cambridge, UK
Synthesis of Azadirachtin: A Long but Successful Journey
Angew. Chem. Int. Ed. 2007, 46: 7629-7632
University of Cambridge, UK
Synthesis of Azadirachtin: A Long but Successful Journey
Angew. Chem. Int. Ed. 2007, 46: 7629-7632
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
23. Januar 2008 (online)
Key words
Claisen rearrangement - radical cyclization - peroxidation - allenes
Significance
Azadirachtin is an insect antifeedant. A major challenge in this 22-year odyssey was the construction of 16 contiguous stereogenic centers seven of which are quaternary. The excerpt depicted here focuses on the Claisen rearrangment used to construct the congested C8-C14 bond.
Comment
Compounds A and G were obtained by total synthesis and by degradation of azadirachtin. The degradation route enabled exploration of the difficult closing stages of the synthesis. Note the harsh conditions required to effect the difficult epoxidation F→G.