Synthesis of functionalized bicyclo[3.1.0]hexanes from aucubin: An access to fused aminocyclopentitols

Treatment of iodolactone 8a, having a cyclopentano[c]pyran skeleton and der iving from aucubin (1) (Scheme I), with sodium trimethylsilanolate permitte d a straightforward rearrangement to bicyclo[3.1.0]hexenes 10a and 10b (Sch emes 3 and 4). Introduction of an N-atom via a modified Curtius reaction pr ovided an easy entry to fused aminocyclopentitols (Schemes 4 and 5). Target 4 is a conformationally restricted cyclopropane-fused analogue of the glyc osidase inhibitors mannostatins A (2) and B (3).