Synthetic study towards azadirachtin: An efficient and stereoselective construction of the AB rings with full functionality

Hidenori Watanabe, Naoki Mori, Daisuke Itoh, Takeshi Kitahara, Kenji Mori

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

(Chemical Equation Presented) From A to B: The decalin moiety of azadirachtin, which includes the fully functionalized AB ring system (see picture), was synthesized stereoselectively in only 23 steps. Key steps include an intramolecular Diels-Alder reaction, a decarboxylation, a Claisen rearrangement, and finally a tandem radical cyclization.

Original languageEnglish
Pages (from-to)1512-1516
Number of pages5
JournalAngewandte Chemie - International Edition
Volume46
Issue number9
DOIs
Publication statusPublished - 2007 Jun 27
Externally publishedYes

Keywords

  • Claisen rearrangement
  • Diels-Alder reaction
  • Natural products
  • Radical reactions

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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