Total syntheses of marrubiin and related labdane diterpene lactones

Yukari Sakagami, Naoki Kondo, Yuki Sawayama, Hiroyuki Yamakoshi, Seiichi Nakamura

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Total syntheses of the labdane diterpene lactones marrubiin, marrulibacetal, desertine, marrulibacetal A, marrubasch F, cyllenine C, marrulanic acid, and marrulactone are described. The trans-decalin moiety of these molecules was constructed in a stereoselective manner by a Pauson-Khand reaction, and the resultant cyclopentenone was oxidatively cleaved for formation of the lactone ring. Elongation of the side chain at C9 was achieved by an epoxide-opening reaction with a variety of nucleophiles, and the functional group manipulations completed the syntheses of these natural products. Stereochemistries of desertine could be established by the transformations.

Original languageEnglish
Article number1610
JournalMolecules
Volume25
Issue number7
DOIs
Publication statusPublished - 2020
Externally publishedYes

Keywords

  • Chiral building block
  • Labdane
  • Marrubiin
  • Pauson-Khand reaction
  • Terpenoid
  • Total synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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