Synthesis of the (4r,5r)-isomer of 5-hydroxy-6-phenyl-4-hexanolide, a lateral root-inducing substance isolated from erwinia quercina

Takeshi Sugai, Hajime Noguchi, Hiromichi Ohta

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Lipase-catalyzed enantioselective lactonization of racemic methyl 6-phenyl-4-hydroxy-5-hexynoate worked well to afford (R)-6-phenyl-5-hexyn-4-olide (42% yield, 81% e.e.). The e.e. of the product was enhanced to 97% by the repetition of enzymatic reaction. From this lactone, (4R,5R)-isomer of 5-hydroxy-6-phenyl-4-hexanolide, a lateral root inducing substance from Erwinia quercina was synthesized via a selective epoxidation of the intermediate and subsequent hydrogenolysis as the keystep.

Original languageEnglish
Pages (from-to)122-126
Number of pages5
JournalBioscience, Biotechnology and Biochemistry
Volume56
Issue number1
DOIs
Publication statusPublished - 1992

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Erwinia
Hydrogenolysis
Epoxidation
Lactones
Lipase
Isomers
4-hexanolide

ASJC Scopus subject areas

  • Biotechnology
  • Molecular Biology
  • Biochemistry
  • Organic Chemistry
  • Analytical Chemistry
  • Applied Microbiology and Biotechnology

Cite this

Synthesis of the (4r,5r)-isomer of 5-hydroxy-6-phenyl-4-hexanolide, a lateral root-inducing substance isolated from erwinia quercina. / Sugai, Takeshi; Noguchi, Hajime; Ohta, Hiromichi.

In: Bioscience, Biotechnology and Biochemistry, Vol. 56, No. 1, 1992, p. 122-126.

Research output: Contribution to journalArticle

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