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

Naoki Mochizuki; Hiroshi Yamada; Takeshi Sugai; Hiromichi Ohta

doi:10.1016/S0968-0896(00)82105-7

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

Naoki Mochizuki, Hiroshi Yamada, Takeshi Sugai, Hiromichi Ohta

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	71-75
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry
Volume	1
Issue number	1
DOIs	https://doi.org/10.1016/S0968-0896(00)82105-7
Publication status	Published - 1993 Jul

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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AU - Sugai, Takeshi

AU - Ohta, Hiromichi

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

Abstract

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