A Total Synthesis of the Antifungal Deoxyaminocyclitol Nabscessin B from L-(+)-Tartaric Acid

Aminocyclitol 2, a recently isolated and notable antifungal agent, was prepared from homochiral γ-hydroxycyclohexenone 4, which is itself available in six steps from l-(+)-tartaric acid (3). The well-defined rigidifying effect arising from the 1,2-diacetal protecting group associated with compound 4 and its derivatives allows for high levels of regio- and stereo-chemical control in the manipulation of the cyclitol framework.