Systematic deletions of the functional groups on amphotercicin B (AmB) have led to the understanding that the mycosamine appendage is absolutely critical for its mechanism of action.  To refine this understanding to the atomistic level, we have targeted AmB's conspicuous C2' hydroxyl group for deletion.  Two synthetic strategies were designed to allow access to C2'deoxy AmB and to other potential derivatives.  The first strategy employs an effective degradative route from the natural product via an electronically tunable site-selective acylation that enables the functionalization of a single hydroxyl group. The second strategy demonstrates the efficacy of a hybrid approach involving the glycosylation of the AmB derived aglycone to the synthetic C2'deoxy mycosamine donor.

Synthesis of C2'deoxy amphotericin B

246th National Meeting (2013)

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