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Diastereoselective Nitrenium Ion-Mediated Cyclofunctionalization: Total Synthesis of (+)-Castanospermine

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journal contribution
posted on 19.11.2010, 00:00 by Edward G. Bowen, Duncan J. Wardrop
The asymmetric total synthesis of the α-glucosidase inhibitor (+)-castanospermine is reported. The central theme in our approach to this polyhydroxylated alkaloid is the simultaneous generation of the piperidine ring and the C-1/8a erythro stereodiad through the diastereoselective, oxamidation of an unsaturated O-alkyl hydroxamate. This process is believed to proceed sequentially via singlet acylnitrenium and aziridinium ion intermediates.