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

Uwe Rinner, Peter Siengalewicz, Tomas Hudlicky

Research output: Contribution to journalArticle

47 Citations (Scopus)

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 languageEnglish
Pages (from-to)115-117
Number of pages3
JournalOrganic Letters
Volume4
Issue number1
DOIs
Publication statusPublished - Jan 10 2002

Fingerprint

nucleophiles
Cyclization
toluene
sulfates
Lewis Acids
Nucleophiles
oxidation
acids
oxygen
synthesis
matrices
Sulfates
Oxygen
Oxidation
epi-7-deoxypancratistatin
bromobenzene
phenanthridone
toluene dioxygenase
aziridine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization. / Rinner, Uwe; Siengalewicz, Peter; Hudlicky, Tomas.

In: Organic Letters, Vol. 4, No. 1, 10.01.2002, p. 115-117.

Research output: Contribution to journalArticle

Rinner, Uwe ; Siengalewicz, Peter ; Hudlicky, Tomas. / Total synthesis of epi-7-deoxypancratistatin via aza-payne rearrangement and intramolecular cyclization. In: Organic Letters. 2002 ; Vol. 4, No. 1. pp. 115-117.
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