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Synthesis of polyhydroxycyclohexanes and relatives from (-)-quinic acid
Concepción González1, Montserrat Carballido, Luis Castedo
1Departamento de Química Orgánica y Unidad Asociada al C.S.I.C., Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain. cgb1@lugo.usc.es
Abstract:
An efficient and versatile strategy for the synthesis of polyhydroxycyclohexanes and related compounds 3-6 is reported. The successful synthesis of these analogues has been achieved from a common intermediate, quinic acid derived lactone 2, rapidly accessible from cheap and commercially available (-)-quinic acid (1) as a chiral template. A practical route involving stereocontrolled epoxide formation and hydrolysis has been developed for the synthesis of 2,3-trans analogues 3 and 4. The preparation of the 2,3-cis analogues 5 and 6 has been realized by diasteroselective oxidation of a 5,6-double bond.