Stereodivergent synthesis and relative stereostructure of the C1-C13 fragment of symbiodinolide

Hiroyoshi Takamura, Hiroko Wada, Mao Ogino, Takahiro Kikuchi, Isao Kadota, Daisuke Uemura

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Four possible diastereomers of the C1-C13 fragment of symbiodinolide, which were proposed by the stereostructural analysis of the degraded product, were synthesized in a stereodivergent and stereoselective manner. The key transformations were aldol reaction of methyl acetoacetate with the aldehyde, diastereoselective reduction of the resulting β-hydroxy ketone, and the stereoinversion at the C6 position. Comparison of the 1H NMR data between the four synthetic products and the degraded product revealed the relative stereostructure of the C1-C13 fragment of symbiodinolide.

Original languageEnglish
Pages (from-to)3111-3123
Number of pages13
JournalJournal of Organic Chemistry
Volume80
Issue number6
DOIs
Publication statusPublished - Mar 20 2015

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Ketones
Aldehydes
Nuclear magnetic resonance
symbiodinolide
methyl acetoacetate
3-hydroxybutanal
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Stereodivergent synthesis and relative stereostructure of the C1-C13 fragment of symbiodinolide. / Takamura, Hiroyoshi; Wada, Hiroko; Ogino, Mao; Kikuchi, Takahiro; Kadota, Isao; Uemura, Daisuke.

In: Journal of Organic Chemistry, Vol. 80, No. 6, 20.03.2015, p. 3111-3123.

Research output: Contribution to journalArticle

Takamura, Hiroyoshi ; Wada, Hiroko ; Ogino, Mao ; Kikuchi, Takahiro ; Kadota, Isao ; Uemura, Daisuke. / Stereodivergent synthesis and relative stereostructure of the C1-C13 fragment of symbiodinolide. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 6. pp. 3111-3123.
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