A synthesis of (R-recifeiolide by the aid of biochemical reaction as the key-step

Naoki Mochizuki, Hiroshi Yamada, Takeshi Sugai, Hiromichi Ohta

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

(R)-Recifeiolide, a naturally occurring macrolactone, was synthesized in optically pure form by the aid of biocatalysts. Lipase-catalyzed lactonization of the racemic precursor afforded the desired compound with a concomitant kinetic resolution. The optically active acyclic precursor could be synthesized by the reduction of corresponding ketone with Pichia farinosa IAM 4682. The yeast reduction proceeded with the anti-Prelog rule, selecting si-face attack on the carbonyl group to give (R)-alcohol with > 95% e.e.

Original languageEnglish
Pages (from-to)71-75
Number of pages5
JournalBioorganic and Medicinal Chemistry
Volume1
Issue number1
DOIs
Publication statusPublished - 1993

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Pichia
Ketones
Lipase
Yeasts
Alcohols
Enzymes
Yeast
Kinetics
recifeiolide

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

A synthesis of (R-recifeiolide by the aid of biochemical reaction as the key-step. / Mochizuki, Naoki; Yamada, Hiroshi; Sugai, Takeshi; Ohta, Hiromichi.

In: Bioorganic and Medicinal Chemistry, Vol. 1, No. 1, 1993, p. 71-75.

Research output: Contribution to journalArticle

Mochizuki, Naoki ; Yamada, Hiroshi ; Sugai, Takeshi ; Ohta, Hiromichi. / A synthesis of (R-recifeiolide by the aid of biochemical reaction as the key-step. In: Bioorganic and Medicinal Chemistry. 1993 ; Vol. 1, No. 1. pp. 71-75.
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