Enantioselective stereodivergent approach to α-hydroxy skipped dienes: Synthesis of the western polyene fragment of corallopyronin A

Yoshiyuki Nagashima, Yuto Okada, Takaaki Sato, Noritaka Chida

Research output: Contribution to journalArticle

Abstract

Synthesis of the western polyene fragment of corallopyronin A is documented. The α-hydroxy skipped diene structure is stereoselectively synthesized by our method consisting of enantioselective allenylation of an aldehyde, hydroboration of the resulting 1, 1-disubstituted allene and Migita-Kosugi-Stille coupling. The developed approach could become a general platform for α-hydroxy skipped dienes embedded in a number of biologically active natural products because all eight stereoisomers of the α-hydroxy skipped diene are potentially available from the same aldehyde through these three stereodivergent reactions.

Original languageEnglish
Pages (from-to)1519-1521
Number of pages3
JournalChemistry Letters
Volume48
Issue number12
DOIs
Publication statusPublished - 2019 Jan 1

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Polyenes
Aldehydes
Stereoisomerism
Biological Products
corallopyronin A
propadiene

Keywords

  • Allene
  • Hydroboration
  • Skipped diene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Enantioselective stereodivergent approach to α-hydroxy skipped dienes : Synthesis of the western polyene fragment of corallopyronin A. / Nagashima, Yoshiyuki; Okada, Yuto; Sato, Takaaki; Chida, Noritaka.

In: Chemistry Letters, Vol. 48, No. 12, 01.01.2019, p. 1519-1521.

Research output: Contribution to journalArticle

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