Total synthesis of (-)-Haouamine B pentaacetate and structural revision of haouamine B

Yuichi Momoi, Kei Ichiro Okuyama, Hiroki Toya, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused β-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the β-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubía.

Original languageEnglish
Pages (from-to)13215-13219
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number48
DOIs
Publication statusPublished - 2014 Nov 24

Keywords

  • Alkaloids
  • Aromatic substitution
  • Cross-coupling
  • Cyclization
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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