Enantioselective Total Synthesis of (+)-Neostenine

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

Research output: Contribution to journalArticle

19 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
JournalChemistry - A European Journal
DOIs
Publication statusAccepted/In press - 2016

Fingerprint

Lactams
Chirality
Polyols
Cyclization
polyol

Keywords

  • Alkaloid
  • Allylic compound
  • Diol
  • Sigmatropic rearrangement
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantioselective Total Synthesis of (+)-Neostenine. / Nakayama, Yasuaki; Maeda, Yuichiro; Kotatsu, Masayuki; Sekiya, Ruriko; Ichiki, Masato; Satou, Takaaki; Chida, Noritaka.

In: Chemistry - A European Journal, 2016.

Research output: Contribution to journalArticle

Nakayama, Yasuaki ; Maeda, Yuichiro ; Kotatsu, Masayuki ; Sekiya, Ruriko ; Ichiki, Masato ; Satou, Takaaki ; Chida, Noritaka. / Enantioselective Total Synthesis of (+)-Neostenine. In: Chemistry - A European Journal. 2016.
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AU - Satou, Takaaki

AU - Chida, Noritaka

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