The 5-Endo-trig Cyclization of D-Glucose Derived γ-Alkenylamines with Mercury (II) Salts: Synthesis of 1-Deoxycastanospermine and its 8a-epi-Analogueâ€

Abstract

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).

Keywords

• Aminosugars
• aminomercuration
• alkaloids
• enzyme inhibitors
• nitrones.