Stereocontrolled synthesis and structural confirmation of the C14 - C24 degraded fragment of symbiodinolide

Hiroyoshi Takamura, Yuichiro Kadonaga, Isao Kadota, Daisuke Uemura

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

The C14-C24 fragment of symbiodinolide possessing the 17R/18R/21R absolute configuration, which was obtained as one of the degraded products of symbiodinolide, and its diastereomer possessing the 17R/18S/21R absolute stereochemistry were synthesized stereoselectively from cis-2-butene-1,4-diol, respectively. The detailed comparison of the synthetic products with the degraded product in the spectroscopic data confirmed unambiguously that the stereostructure of the C14 - C24 fragment was 17R, 18R, and 21R.

Original languageEnglish
Pages (from-to)7569-7576
Number of pages8
JournalTetrahedron
Volume66
Issue number38
DOIs
Publication statusPublished - Sep 18 2010

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Stereochemistry
symbiodinolide
penitricin C

Keywords

  • Polyol macrolide
  • Stereocontrolled synthesis
  • Structural confirmation
  • Symbiodinolide

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereocontrolled synthesis and structural confirmation of the C14 - C24 degraded fragment of symbiodinolide. / Takamura, Hiroyoshi; Kadonaga, Yuichiro; Kadota, Isao; Uemura, Daisuke.

In: Tetrahedron, Vol. 66, No. 38, 18.09.2010, p. 7569-7576.

Research output: Contribution to journalArticle

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