Brewers' yeast-mediated synthesis of (1S,2S)-1-(2-thienyl)-1,2-propanediol and a study on the lipase-catalyzed regioselective introduction of acyl protective group to the diol moiety

Naoki Mochizuki, Takeshi Sugai, Hiromichi Ohta, Tsutomu Yokomatsu, Shiroshi Shibuya

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Abstract

Reductive homologation of thiophenecarboxyaldehyde mediated by brewers' yeast and subsequent recrystallization provided (1S,2S)-1-(2-thienyl)-1,2-propanediol in 29% yield. A Pseudomonas lipase-catalyzed acetylation preferentially occurred on the hydroxyl group at C-1 position of the diol.

Original languageEnglish
Pages (from-to)331-338
Number of pages8
JournalHeterocycles
Volume45
Issue number2
Publication statusPublished - 1997

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Acetylation
Propylene Glycol
Pseudomonas
Lipase
Hydroxyl Radical
Yeast
Saccharomyces cerevisiae

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Brewers' yeast-mediated synthesis of (1S,2S)-1-(2-thienyl)-1,2-propanediol and a study on the lipase-catalyzed regioselective introduction of acyl protective group to the diol moiety. / Mochizuki, Naoki; Sugai, Takeshi; Ohta, Hiromichi; Yokomatsu, Tsutomu; Shibuya, Shiroshi.

In: Heterocycles, Vol. 45, No. 2, 1997, p. 331-338.

Research output: Contribution to journalArticle

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