Synthesis and structural determination of the C33-C42 fragment of symbiodinolide

Hiroyoshi Takamura, Yuichiro Kadonaga, Yoshi Yamano, Chunguang Han, Yoko Aoyama, Isao Kadota, Daisuke Uemura

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Symbiodinolide (1) is a polyol macrolide with a molecular weight of 2859 mu. As one of the degradation reactions, cross-metathesis of 2, which is a methyl ester of 1, with ethylene was performed to give the C33-C42 degraded fragment 4. The absolute configuration of 4 was estimated to be (36S,40S) by Mosher method. Stereoselective synthesis of 4 was achieved in 14 steps from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters exhibited the spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded fragment 4. Thus, the absolute stereochemistry of 4 was elucidated to be (36S,40S).

Original languageEnglish
Pages (from-to)863-866
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number8
DOIs
Publication statusPublished - Feb 25 2009

Keywords

  • Absolute configuration
  • Chemical synthesis
  • Cross-metathesis degradation
  • Polyol macrolide
  • Symbiodinolide

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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