Biomimetic total synthesis of (-)-erinacine E

Hideaki Watanabe, Masahisa Nakada*

*この研究の対応する著者

研究成果: Article査読

45 被引用数 (Scopus)

抄録

Biomimetic total synthesis of (-)-erinacine E (1) has been achieved starting from the enantiopure key intermediate, which was prepared via the convergent approach developed by us. The crucial step in this synthesis is an intramolecular aldol reaction driven by the 1,2-migration of a benzoyl group within a compound that was rationally designed to prevent the retro-aldol reaction, thereby successfully providing the strained skeleton of 1. Considering the structure of a putative biosynthetic intermediate, striatal A, the intramolecular aldol reaction driven by the C4′ acetyl group could be involved in the biosynthesis of 1. This acyl group migratory ring-closing reaction could be applied to the synthesis of other strained molecules.

本文言語English
ページ(範囲)1150-1151
ページ数2
ジャーナルJournal of the American Chemical Society
130
4
DOI
出版ステータスPublished - 2008 1月 30

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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