Enantioselective Total Synthesis of (+)-Neostenine

Yasuaki Nakayama, Yuichiro Maeda, Masayuki Kotatsu, Ruriko Sekiya, Masato Ichiki, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticlepeer-review

28 Citations (Scopus)

Abstract

A chirality transfer approach using acyclic polyol intermediates for the synthesis of (+)-neostenine (1) has been developed. The sequential Overman/Claisen rearrangement of an allylic 1,2-diol was especially useful, installing two contiguous stereocenters with complete diastereoselectivity in a one-pot sequence. The SmI2-mediated cyclization and the subsequent chemoselective reduction of a lactam moiety accomplished the first enantioselective total synthesis of (+)-neostenine (1).

Original languageEnglish
Pages (from-to)3300-3303
Number of pages4
JournalChemistry - A European Journal
Volume22
Issue number10
DOIs
Publication statusPublished - 2016 Mar 1

Keywords

  • alkaloid
  • allylic compound
  • diol
  • sigmatropic rearrangement
  • total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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