Concise chemoenzymatic synthesis of epi-inositol

Carbohydrate Research
Cecilia VitelioDavid Gonzalez

Abstract

epi-Inositol was synthesized in six steps in 40% overall yield from a bacterial bromobenzene metabolite. The chemoenzymatic route involved toluene dioxygenase oxidation, substrate-directed catalytic osmylation, m-CPBA epoxidation, radical debromination, and Amberlite-catalized hydrolysis. The route described is amenable to scaleup and could allow access to cis-inositol, and deoxy derivatives of epi-inositol.

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Citations

Jun 3, 2011·Chemical Reviews·Jan DuchekTomas Hudlicky
Jun 28, 2008·The Journal of Organic Chemistry·Margarita Brovetto, Gustavo Seoane

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