Stereoselective synthesis and absolute configuration of the C33-C42 fragment of symbiodinolide

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

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Cross-metathesis of methyl ester which was prepared from symbiodinolide with ethylene was performed to give the C33-C42 degraded fragment. This fragment was estimated to be (36S,40S)-diol by the modified Mosher method. Stereoselective synthesis of the (36S,40S)-diol and its diastereomer (36R,40S)-diol was achieved from l-aspartic acid. Synthetic bis-(S)- and (R)-MTPA esters which were derivatized from the (36S,40S)-diol exhibited spectroscopic data identical with those of bis-(S)- and (R)-MTPA esters derived from the degraded product. Thus, the absolute stereochemistry of the C33-C42 fragment was elucidated to be (36S,40S).

Original languageEnglish
Pages (from-to)7449-7456
Number of pages8
JournalTetrahedron
Volume65
Issue number36
DOIs
Publication statusPublished - Sep 5 2009

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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