Abstract
(matrix presented) 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.
| Original language | English |
|---|---|
| Pages (from-to) | 115-117 |
| Number of pages | 3 |
| Journal | Organic Letters |
| Volume | 4 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 10 2002 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Rinner, U., Siengalewicz, P., & Hudlicky, T. (2002). Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization. Organic Letters, 4(1), 115-117. https://doi.org/10.1021/ol0169877