Asymmetric formal synthesis of azadirachtin

Naoki Mori, Takeshi Kitahara, Kenji Mori, Hidenori Watanabe

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

An asymmetric formal synthesis of azadirachtin, a potent insect antifeedant, was accomplished in 30 steps to Ley's synthetic intermediate (longest linear sequence). The synthesis features: 1) rapid access to the optically active right-hand segment starting from the known 5-hydroxymethyl-2-cyclopentenone scaffold; 2) construction of the B and E rings by a key intramolecular tandem radical cyclization; 3) formation of the hemiacetal moiety in the C ring through the α-oxidation of the six-membered lactone followed by methanolysis. The asymmetric formal synthesis of azadirachtin (1) was accomplished by utilizing the tandem radical cyclization reaction as a key step. The route to the key intermediate 2 requires the longest linear sequence of 30 steps.

Original languageEnglish
Pages (from-to)14920-14923
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number49
DOIs
Publication statusPublished - 2015 Jan 1
Externally publishedYes

Keywords

  • acetals
  • cyclizations
  • natural products
  • radicals
  • stereoselectivity

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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