Stereocontrolled synthesis of spirosuccinimide derivative of (+)-hydantocidin

Article abstract of DOI:10.1016/0040-4020(94)01027-W

Synthesis of the spirosuccinimide derivative of (+)-hydantocidin 2 is reported. The key step is a SnCl₄-promoted C-glycosidation of the protected D-psicose 3 with allyltrimethylsilane in dichloromethane, which proceeded in good yield and high selectivity; however, C-glycosidation of 3 in acetonitrile afforded the spirooxazoline 6. Synthesis of 2 was achieved in 13% overall yield from 3.