The 5-Endo-trig Cyclization of d-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxy-castanospermine and its 8a-epi-Analogue

摘要

The intramolecular aminomercuration of γ-alkenylamines >1a, >1b and >4 was shown to afford the 5-endo-trig cyclized product exclusively in good yield. The utility of pyrrolidine derivatives thus obtained from D-glucose derived γ-alkenylamines >1a and >1b was demonstrated in the synthesis of 1-deoxycastanospermine (>3a) and 1-deoxy-8a-epi-castanospermine (>3b).