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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980585 | PMC |
| http://dx.doi.org/10.1021/ol102371x | DOI Listing |
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