Preparative bioorganic chemistry; XIV. Preparation of (2S,3S)-1-phenylthio-2,3-pentanediol and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol by yeast reduction of the corresponding diketones, and conversion of the former to (+)-endo-brevicomin

K. Mori; M. Ishikura; Y. B. Seu

doi:10.1055/s-1991-26502

Preparative bioorganic chemistry; XIV. Preparation of (2S,3S)-1-phenylthio-2,3-pentanediol and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol by yeast reduction of the corresponding diketones, and conversion of the former to (+)-endo-brevicomin

K. Mori
, M. Ishikura
, Y. B. Seu

School of Life Science and Biotechnology

The University of Tokyo

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

7 Scopus citations

Abstract

(2S,3S)-1-Phenylthio-2,3-pentanediol (2) and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol (16) were prepared by reducing the corresponding diketones, 6 and 15, with baker's yeast. Conversion of 2 to (3S,4R)-8-nonene-3,4-diol (13), the key intermediate for the synthesis of (+)-endo-brevicomin [endo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane, (1R,5S,7S)-1], is also described.

Original language	English
Pages (from-to)	487-490
Number of pages	4
Journal	Synthesis
Issue number	6
DOIs	https://doi.org/10.1055/s-1991-26502
State	Published - 1991

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@article{2cf6aecd7cb34c71ae728b87ecbb2207,

title = "Preparative bioorganic chemistry; XIV. Preparation of (2S,3S)-1-phenylthio-2,3-pentanediol and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol by yeast reduction of the corresponding diketones, and conversion of the former to (+)-endo-brevicomin",

abstract = "(2S,3S)-1-Phenylthio-2,3-pentanediol (2) and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol (16) were prepared by reducing the corresponding diketones, 6 and 15, with baker's yeast. Conversion of 2 to (3S,4R)-8-nonene-3,4-diol (13), the key intermediate for the synthesis of (+)-endo-brevicomin [endo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane, (1R,5S,7S)-1], is also described.",

author = "K. Mori and M. Ishikura and Seu, \{Y. B.\}",

year = "1991",

doi = "10.1055/s-1991-26502",

language = "English",

pages = "487--490",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

number = "6",

}

Preparative bioorganic chemistry; XIV. Preparation of (2S,3S)-1-phenylthio-2,3-pentanediol and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol by yeast reduction of the corresponding diketones, and conversion of the former to (+)-endo-brevicomin. / Mori, K.; Ishikura, M.; Seu, Y. B.
In: Synthesis, No. 6, 1991, p. 487-490.

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

TY - JOUR

T1 - Preparative bioorganic chemistry; XIV. Preparation of (2S,3S)-1-phenylthio-2,3-pentanediol and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol by yeast reduction of the corresponding diketones, and conversion of the former to (+)-endo-brevicomin

AU - Mori, K.

AU - Ishikura, M.

AU - Seu, Y. B.

PY - 1991

Y1 - 1991

N2 - (2S,3S)-1-Phenylthio-2,3-pentanediol (2) and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol (16) were prepared by reducing the corresponding diketones, 6 and 15, with baker's yeast. Conversion of 2 to (3S,4R)-8-nonene-3,4-diol (13), the key intermediate for the synthesis of (+)-endo-brevicomin [endo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane, (1R,5S,7S)-1], is also described.

AB - (2S,3S)-1-Phenylthio-2,3-pentanediol (2) and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol (16) were prepared by reducing the corresponding diketones, 6 and 15, with baker's yeast. Conversion of 2 to (3S,4R)-8-nonene-3,4-diol (13), the key intermediate for the synthesis of (+)-endo-brevicomin [endo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]octane, (1R,5S,7S)-1], is also described.

UR - https://www.scopus.com/pages/publications/0025777956

U2 - 10.1055/s-1991-26502

DO - 10.1055/s-1991-26502

M3 - Article

AN - SCOPUS:0025777956

SN - 0039-7881

SP - 487

EP - 490

JO - Synthesis

JF - Synthesis

IS - 6

ER -

Preparative bioorganic chemistry; XIV. Preparation of (2S,3S)-1-phenylthio-2,3-pentanediol and (2S,3S)-1-phenylsulfonyl-2,3-pentanediol by yeast reduction of the corresponding diketones, and conversion of the former to (+)-endo-brevicomin

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