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Concise chemoenzymatic synthesis of epi-inositol
Cecilia Vitelio1, Ana Bellomo, Margarita Brovetto
1Departamento de Química Orgánica, Facultad de Química, Universidad de la República, C.C. 1157, Montevideo, Uruguay.
Carbohydrate Research
|June 29, 2004
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.