Total synthesis of epi-7-deoxypancratistatin via aza-Payne rearrangement and intramolecular cyclization

Uwe Rinner; Peter Siengalewicz; Tomas Hudlicky

doi:10.1021/ol0169877

Total synthesis of epi-7-deoxypancratistatin via aza-Payne rearrangement and intramolecular cyclization

Org Lett. 2002 Jan 10;4(1):115-7. doi: 10.1021/ol0169877.

Authors

Uwe Rinner¹, Peter Siengalewicz, Tomas Hudlicky

Affiliation

¹ Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.

PMID: 11772104
DOI: 10.1021/ol0169877

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkaloids / chemical synthesis*
Amaryllidaceae Alkaloids*
Antineoplastic Agents / chemical synthesis*
Aza Compounds / chemical synthesis
Cyclization
Indicators and Reagents
Isoquinolines / chemical synthesis*
Magnetic Resonance Spectroscopy
Magnoliopsida

Substances

Alkaloids
Amaryllidaceae Alkaloids
Antineoplastic Agents
Aza Compounds
Indicators and Reagents
Isoquinolines
epi-7-deoxypancratistatin