Efficient Synthesis of (-)-Hanishin, (-)-Longamide B, and (-)-Longamide B Methyl Ester through Piperazinone Formation from 1,2-Cyclic Sulfamidates

Zenyu Shiokawa, Shinsuke Inuki, Koichi Fukase, Yukari Fujimoto

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

We describe a simple chiral-pool synthesis of (-)-longamide B, (-)-longamide B methyl ester, and (-)-hanishin. The key feature of the total synthesis is the formation of a piperazinone from a 1,2-cyclic sulfamidate and methyl 2-pyrrolecarboxylate, which permits efficient construction of the pyrrolopiperazinone core scaffold.

Original languageEnglish
Article numberst-2015-u0727-l
Pages (from-to)616-620
Number of pages5
JournalSynlett
Volume27
Issue number4
DOIs
Publication statusPublished - 2016 Mar 1

Keywords

  • asymmetric synthesis
  • hanishin
  • heterocycles
  • longamide B
  • piperazinones
  • sulfamidates

ASJC Scopus subject areas

  • Organic Chemistry

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