Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-l,2,3-triol toward the total synthesis of aquayamycin

T. Matsumoto; T. Konegawa; H. Yamaguchi; T. Nakamura; T. Sugai; K. Suzuki

doi:10.1055/s-2001-17487

Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-l,2,3-triol toward the total synthesis of aquayamycin

T. Matsumoto, T. Konegawa, H. Yamaguchi, T. Nakamura, T. Sugai, K. Suzuki

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

8 Citations (Scopus)

Abstract

The diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol was efficiently asymmetrized by hydrolysis with Candida antarctica lipase to give the corresponding mono-acetate in enantiomerically pure form, which was used as the starting material for the total synthesis of aquayamycin. Application of the protocol to the related cyclohexanetriols is also described.

Original language	English
Pages (from-to)	1650-1652
Number of pages	3
Journal	Synlett
Issue number	10
DOIs	https://doi.org/10.1055/s-2001-17487
Publication status	Published - 2001
Externally published	Yes

Keywords

Asymmetrization
Enzyme
Hydrolysis
Meso compound
Total synthesis

ASJC Scopus subject areas

Organic Chemistry

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title = "Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-l,2,3-triol toward the total synthesis of aquayamycin",

abstract = "The diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol was efficiently asymmetrized by hydrolysis with Candida antarctica lipase to give the corresponding mono-acetate in enantiomerically pure form, which was used as the starting material for the total synthesis of aquayamycin. Application of the protocol to the related cyclohexanetriols is also described.",

keywords = "Asymmetrization, Enzyme, Hydrolysis, Meso compound, Total synthesis",

author = "T. Matsumoto and T. Konegawa and H. Yamaguchi and T. Nakamura and T. Sugai and K. Suzuki",

year = "2001",

doi = "10.1055/s-2001-17487",

language = "English",

pages = "1650--1652",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-l,2,3-triol toward the total synthesis of aquayamycin

AU - Matsumoto, T.

AU - Konegawa, T.

AU - Yamaguchi, H.

AU - Nakamura, T.

AU - Sugai, T.

AU - Suzuki, K.

PY - 2001

Y1 - 2001

N2 - The diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol was efficiently asymmetrized by hydrolysis with Candida antarctica lipase to give the corresponding mono-acetate in enantiomerically pure form, which was used as the starting material for the total synthesis of aquayamycin. Application of the protocol to the related cyclohexanetriols is also described.

AB - The diacetate of meso-2-(2-propynyl)cyclohexane-1,2,3-triol was efficiently asymmetrized by hydrolysis with Candida antarctica lipase to give the corresponding mono-acetate in enantiomerically pure form, which was used as the starting material for the total synthesis of aquayamycin. Application of the protocol to the related cyclohexanetriols is also described.

KW - Asymmetrization

KW - Enzyme

KW - Hydrolysis

KW - Meso compound

KW - Total synthesis

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DO - 10.1055/s-2001-17487

M3 - Article

AN - SCOPUS:0034805351

SN - 0936-5214

SP - 1650

EP - 1652

JO - Synlett

JF - Synlett

IS - 10

ER -

Lipase-catalyzed asymmetrization of diacetate of meso-2-(2-propynyl)cyclohexane-l,2,3-triol toward the total synthesis of aquayamycin

Abstract

Keywords

ASJC Scopus subject areas

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