Issue 10, 1994

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

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1994, 1247-1248

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

N. Chida, T. Tanikawa, T. Tobe and S. Ogawa, J. Chem. Soc., Chem. Commun., 1994, 1247 DOI: 10.1039/C39940001247

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