Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy

Oxidative
allene amination provides rapid access to densely functionalized
amine-containing stereotriads through highly reactive bicyclic methylene­aziridine
intermediates. This strategy has been demonstrated as a viable approach
for the construction of the densely functionalized aminocyclitol core
of jogyamycin, a natural product with potent antiprotozoal activity.
Importantly, the flexibility of oxidative allene amination will enable
the syntheses of modified aminocyclitol analogues of the jogyamycin
core.