Synthetic research on cyclitols using C6-chiron, 6-(benzyloxy)-3- cyclohexen-1-ol: A concise and highly diastereoselective synthesis of (-)- gala-quercitol

Article abstract of DOI:10.1016/S0040-4039(99)00608-5

Transformation of a C₆-chiron, 6-(benzyloxy)-3-cyclohexen-1-ol into polyoxygenated cyclohexanes involving a stereodivergen epoxide rearrangement was investigated. An asymmetric synthesis of (-)-gala-quercitol was accomplished via sequential highly diastereoselective epoxidation, base- promoted epoxide rearrangement, and dihydroxylation.