Unified total synthesis, stereostructural elucidation, and biological evaluation of sarcophytonolides

Hiroyoshi Takamura, Isao Kadota

Research output: Contribution to journalArticle

Abstract

Sarcophytonolides are cembranolide diterpenes isolated from the soft corals of genus Sarcophyton since 2005. Herein, unified total synthesis of sarcophytonolides C, E, F, G, H, and J and isosarcophytonolide D is reported. The key transformations in the synthetic route are fragment coupling, alkoxycarbonylallylation, macrolactonization, and transannular ring - closing metathesis. These total syntheses resulted in the absolute stereochemical confirmation of sarcophytonolide H, determination of sarcophytonolides C, E, F, and G, and revision of sarcophytonolide J and isosarcophytonolide D. We also evaluated the antifouling activity and toxicity of the synthetic sarcophytonolides H and J and their analogues as well as the cytotoxicity of the synthetic sarcophytonolides and their key synthetic intermediates.

Original languageEnglish
Pages (from-to)1190-1200
Number of pages11
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume77
Issue number12
DOIs
Publication statusPublished - 2019

Keywords

  • Alkoxycarbonylallylation
  • Antifouling activity
  • Biological evaluation
  • Cembranolide
  • Cytotoxity
  • Diterpene
  • Fragment coupling
  • Macrolactonization
  • Sarcophytonolide
  • Structural elucidation
  • Toxicity
  • Transannular ring-closing metathesis
  • Unified total synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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