The 5-endo-trig cyclization of D-glucose derived γ-alkenylamines with mercury (II) salts: synthesis of 1-deoxycastanospermine and its 8a-epi-analogue

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).