Stereoselective Synthesis of the Proposed C79-C104 Fragment of Symbiodinolide

Hiroyoshi Takamura, Takayuki Fujiwara, Yohei Kawakubo, Isao Kadota, Daisuke Uemura

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Stereoselective and streamlined synthesis of the proposed C79-C104 fragment 2 of symbiodinolide (1), a polyol marine natural product with a molecular weight of 2860, was achieved. In the synthetic route, the proposed C79-C104 fragment 2 was synthesized by utilizing a Julia-Kocienski olefination and subsequent Sharpless asymmetric dihydroxylation as key transformations in a convergent manner. Detailed comparison of the 13C NMR chemical shifts between the natural product and the synthetic C79-C104 fragment 2 revealed that the stereostructure at the C91-C99 carbon chain moiety of symbiodinolide (1) should be reinvestigated.

Original languageEnglish
Pages (from-to)1979-1983
Number of pages5
JournalChemistry - A European Journal
Volume22
Issue number6
DOIs
Publication statusPublished - Feb 5 2016

Keywords

  • macrocycles
  • natural products
  • polyols
  • stereoselective synthesis
  • structure elucidation

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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