Concise chemoenzymatic synthesis of epi-inositol.
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.
Vitelio
Cecilia
C
Departamento de Química Orgánica, Facultad de Química, Universidad de la República, C.C. 1157, Montevideo, Uruguay.
Bellomo
Ana
A
Brovetto
Margarita
M
Seoane
Gustavo
G
Gonzalez
David
D
D001969:Bromobenzenes / Q000737:chemistry*; D002384:Catalysis; D002725:Chloroform; D004852:Epoxy Compounds / Q000737:chemistry; D006868:Hydrolysis; D007294:Inositol / Q000138:chemical synthesis / Q000737:chemistry*; D008956:Models, Chemical; D010100:Oxygen / Q000378:metabolism; D010105:Oxygenases / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D001969:Bromobenzenes; D004852:Epoxy Compounds; D007294:Inositol; D002725:Chloroform; C032036:bromobenzene; D010105:Oxygenases; C023172:toluene dioxygenase; D010100:Oxygen