Synthesis of (+)-galactostatin and (+)-1-deoxygalactostatin utilizing L-quebrachitol as a chiral building block

Noritaka Chida; Tetsuya Tanikawa; Takahiko Tobe; Seiichiro Ogawa

doi:10.1039/C39940001247

Synthesis of (+)-galactostatin and (+)-1-deoxygalactostatin utilizing L-quebrachitol as a chiral building block

Noritaka Chida, Tetsuya Tanikawa, Takahiko Tobe, Seiichiro Ogawa

Department of Applied Chemistry

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

28 Citations (Scopus)

Abstract

The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 1, into galactosidase inhibitors, (+)-galactostatin 2 and (+)-1-deoxygalactostatin 3 is described; the key steps in this synthesis are (i) stereoselective introduction of an azido function and (ii) regioselective ring cleavage of the cyclohexane ring of 1 by way of the Baeyer-Villiger reaction.

Original language	English
Pages (from-to)	1247-1248
Number of pages	2
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	10
DOIs	https://doi.org/10.1039/C39940001247
Publication status	Published - 1994 Dec 1

ASJC Scopus subject areas

Molecular Medicine

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abstract = "The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 1, into galactosidase inhibitors, (+)-galactostatin 2 and (+)-1-deoxygalactostatin 3 is described; the key steps in this synthesis are (i) stereoselective introduction of an azido function and (ii) regioselective ring cleavage of the cyclohexane ring of 1 by way of the Baeyer-Villiger reaction.",

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AU - Tobe, Takahiko

AU - Ogawa, Seiichiro

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N2 - The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 1, into galactosidase inhibitors, (+)-galactostatin 2 and (+)-1-deoxygalactostatin 3 is described; the key steps in this synthesis are (i) stereoselective introduction of an azido function and (ii) regioselective ring cleavage of the cyclohexane ring of 1 by way of the Baeyer-Villiger reaction.

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Synthesis of (+)-galactostatin and (+)-1-deoxygalactostatin utilizing L-quebrachitol as a chiral building block

Abstract

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