Toward the synthesis of γ-pyrone-containing natural products: Diastereoselective aldol-type reaction of a γ-pyrone

Takuma Takemura, Ichiro Hayakawa, Emi Fukasawa, Tetsuya Sengoku, Hideo Kigoshi

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The diastereoselective aldol-type reaction of a γ-pyrone via a sodium anion has been developed. This reaction is useful for synthesizing γ-pyrone-containing natural products. Also, we applied the Mukaiyama aldol-type reaction of silyl enol ether of γ-pyrone by using TiCl 4. This Mukaiyama aldol-type reaction of γ-pyrone indicated higher anti-aldol selectivity than the aldol-type reaction of a γ-pyrone with NaHMDS.

Original languageEnglish
Pages (from-to)6477-6484
Number of pages8
JournalTetrahedron
Volume68
Issue number32
DOIs
Publication statusPublished - Aug 12 2012
Externally publishedYes

Keywords

  • Diastereoselective aldol-type reaction of a γ-pyrone
  • Mukaiyama aldol-type reaction of a γ-pyrone
  • anti-Aldol selectivity

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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