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Concise chemoenzymatic synthesis of epi-inositol

2004; Elsevier BV; Volume: 339; Issue: 10 Linguagem: Inglês

10.1016/j.carres.2004.04.011

1873-426X

Cecilia Vitelio, Ana Bellomo, Margarita Brovetto, Gustavo Seoane, David González,

Chemical synthesis and alkaloids

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.