> Details

Ley, Steven V.; Abad‐Somovilla, Antonio; Anderson, James C.; Ayats, Carles; Bänteli, Rolf; Beckmann, Edith; Boyer, Alistair; Brasca, Maria G.; Brice, Abigail; Broughton, Howard B.; Burke, Brenda J.; Cleator, Ed; Craig, Donald; Denholm, Alastair A.; Denton, Ross M.; Durand‐Reville, Thomas; Gobbi, Luca B.; Göbel, Michael; Gray, Brian Lawrence; Grossmann, Robert B.; Gutteridge, Claire E.; Hahn, Norbert; Harding, Sarah L.; Jennens, David C.; [...]

The Synthesis of Azadirachtin: A Potent Insect Antifeedant

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  • Media type: E-Article
  • Title: The Synthesis of Azadirachtin: A Potent Insect Antifeedant
  • Contributor: Ley, Steven V.; Abad‐Somovilla, Antonio; Anderson, James C.; Ayats, Carles; Bänteli, Rolf; Beckmann, Edith; Boyer, Alistair; Brasca, Maria G.; Brice, Abigail; Broughton, Howard B.; Burke, Brenda J.; Cleator, Ed; Craig, Donald; Denholm, Alastair A.; Denton, Ross M.; Durand‐Reville, Thomas; Gobbi, Luca B.; Göbel, Michael; Gray, Brian Lawrence; Grossmann, Robert B.; Gutteridge, Claire E.; Hahn, Norbert; Harding, Sarah L.; Jennens, David C.; [...]
  • imprint: Wiley, 2008
  • Published in: Chemistry – A European Journal
  • Language: English
  • DOI: 10.1002/chem.200801103
  • ISSN: 0947-6539; 1521-3765
  • Keywords: General Chemistry ; Catalysis ; Organic Chemistry
  • Origination:
  • Footnote:
  • Description: <jats:title>Abstract</jats:title><jats:p>We describe in full the first synthesis of the potent insect antifeedant azadirachtin through a highly convergent approach. An <jats:italic>O</jats:italic>‐alkylation reaction is used to unite decalin ketone and propargylic mesylate fragments, after which a Claisen rearrangement constructs the central C8C14 bond in a stereoselective fashion. The allene which results from this sequence then enables a second critical carboncarbon bond forming event whereby the [3.2.1] bicyclic system, present in the natural product, is generated via a 5‐<jats:italic>exo</jats:italic>‐radical cyclisation process. Finally, using knowledge gained through our early studies into the reactivity of the natural product, a series of carefully designed steps completes the synthesis of this challenging molecule.</jats:p>