Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide

Hajime Ikeda, Eriko Sato, Takeshi Sugai, Hiromichi Ohta

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.

Original languageEnglish
Pages (from-to)8113-8122
Number of pages10
JournalTetrahedron
Volume52
Issue number24
DOIs
Publication statusPublished - 1996 Jun 10

Fingerprint

Pichia
Ketones
Yeast
Yeasts
Alcohols
Substrates
2,4-pentanediol
2,5-hexanediol

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide. / Ikeda, Hajime; Sato, Eriko; Sugai, Takeshi; Ohta, Hiromichi.

In: Tetrahedron, Vol. 52, No. 24, 10.06.1996, p. 8113-8122.

Research output: Contribution to journalArticle

Ikeda, Hajime ; Sato, Eriko ; Sugai, Takeshi ; Ohta, Hiromichi. / Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide. In: Tetrahedron. 1996 ; Vol. 52, No. 24. pp. 8113-8122.
@article{159205ffb13048d59548547b5591ebb8,
title = "Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide",
abstract = "Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)-2,5-Hexanediol (83{\%} yd., >99{\%} e.e., 95{\%} d.e.), (2R,4R)-2,4-pentanediol (94{\%} yd., >99{\%} e.e., 98{\%} d.e.), and (R)-pentanolide (67{\%} yd., >99{\%} e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.",
author = "Hajime Ikeda and Eriko Sato and Takeshi Sugai and Hiromichi Ohta",
year = "1996",
month = "6",
day = "10",
doi = "10.1016/0040-4020(96)00373-0",
language = "English",
volume = "52",
pages = "8113--8122",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "24",

}

TY - JOUR

T1 - Yeast-mediated synthesis of optically active diols with C2-symmetry and (R)-4-pentanolide

AU - Ikeda, Hajime

AU - Sato, Eriko

AU - Sugai, Takeshi

AU - Ohta, Hiromichi

PY - 1996/6/10

Y1 - 1996/6/10

N2 - Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.

AB - Reduction of some diketones and a ketoacid with yeast, Pichia farinosa IAM 4682 was examined. The reduction of carbonyl groups proceeded highly selectively with an anti-Prelog fashion to give (R)-alcohols. (2R,5R)-2,5-Hexanediol (83% yd., >99% e.e., 95% d.e.), (2R,4R)-2,4-pentanediol (94% yd., >99% e.e., 98% d.e.), and (R)-pentanolide (67% yd., >99% e.e.) were highly efficiently obtained from the corresponding ketones. Effect of the structure of substrate on the stereochemical course as well as the selectivity were discussed.

UR - http://www.scopus.com/inward/record.url?scp=0030006659&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0030006659&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(96)00373-0

DO - 10.1016/0040-4020(96)00373-0

M3 - Article

AN - SCOPUS:0030006659

VL - 52

SP - 8113

EP - 8122

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 24

ER -