First enantioselective synthesis of exiguamide, a nitrogen-containing spirocyclic sesquiterpene isolated from the marine sponge Geodia exigua

Shunsuke Konishi, Yuki Mitani, Naoki Mori, Hirosato Takikawa, Hidenori Watanabe

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

(+)-Exiguamide is a nitrogen-containing spirocyclic sesquiterpene isolated from the marine sponge Geodia exigua. This study aims to report the first synthesis of both enantiomers of exiguamide, featuring the stereoselective intramolecular cyclopropanation and stereoselective homoconjugate addition of azide to cyclopropyl ketone as the key steps.

Original languageEnglish
Pages (from-to)652-657
Number of pages6
JournalTetrahedron
Volume75
Issue number5
DOIs
Publication statusPublished - 2019 Feb 1
Externally publishedYes

Keywords

  • Cyclopropanation
  • Enantioselective synthesis
  • Exiguamide
  • Homoconjugate addition
  • Spirocyclic sesquiterpene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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