RESUMO

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.

Assuntos

Bromobenzenos/química , Inositol/química , Oxigenases/química , Catálise , Clorofórmio , Compostos de Epóxi/química , Hidrólise , Inositol/síntese química , Modelos Químicos , Oxigênio/metabolismo , Estereoisomerismo , Especificidade por Substrato