First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone

Masaaki Matsuda, Takahiro Yamazaki, Ken ichi Fuhshuku, Takeshi Sugai

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

While the first total synthesis of modiolide A (1a), a 10-membered ring lactone with a marine-origin was achieved, an important chiral building block for constructing the chirality at C-4 in 1a, (S)-6-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (3a) was obtained in as high as 96.1% ee. Asymmetric reduction of a silylated propargyl ketone (5) mediated by whole-cell of Pichia minuta IAM 12215 was established. This yeast-mediated reduction was also applicable to provide stereochemically pure (3S,5R)-5-[(4-methoxybenzyl)oxy]-1-trimethylsilyl-1-hexyn-3-ol (15), a synthetic intermediate for the related 10-membered lactone, tuckolide (16).

Original languageEnglish
Pages (from-to)8752-8760
Number of pages9
JournalTetrahedron
Volume63
Issue number36
DOIs
Publication statusPublished - 2007 Sep 3

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Lactones
Ketones
Yeast
Yeasts
Pichia
Chirality
modiolide A
decarestrictine D

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone. / Matsuda, Masaaki; Yamazaki, Takahiro; Fuhshuku, Ken ichi; Sugai, Takeshi.

In: Tetrahedron, Vol. 63, No. 36, 03.09.2007, p. 8752-8760.

Research output: Contribution to journalArticle

Matsuda, Masaaki ; Yamazaki, Takahiro ; Fuhshuku, Ken ichi ; Sugai, Takeshi. / First total synthesis of modiolide A, based on the whole-cell yeast-catalyzed asymmetric reduction of a propargyl ketone. In: Tetrahedron. 2007 ; Vol. 63, No. 36. pp. 8752-8760.
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