U. Rinner, Peter Siengalewicz, T. Hudlický
Jan 10, 2002
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0
Influential Citations
29
Citations
Journal
Organic letters
Abstract
[reaction: see text] epi-7-Deoxypancratistatin containing the cis-fused phenanthridone core was synthesized in 12 steps from bromobenzene. Key features of this synthesis include the enzymatic oxidation of bromobenzene with toluene dioxygenase, selective opening of a cyclic sulfate over an aziridine with oxygen nucleophiles, and an intramolecular Lewis acid-catalyzed cyclization onto an epoxy conduramine derived via aza-Payne rearrangement.