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 Jul

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ASJC Scopus subject areas

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

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