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

Uwe Rinner, Peter Siengalewicz, Tomas Hudlicky^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

51 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 language	English
Pages (from-to)	115-117
Number of pages	3
Journal	Organic Letters
Volume	4
Issue number	1
DOIs	https://doi.org/10.1021/ol0169877
Publication status	Published - Jan 10 2002
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

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AU - Rinner, Uwe

AU - Siengalewicz, Peter

AU - Hudlicky, Tomas

PY - 2002/1/10

Y1 - 2002/1/10

N2 - (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.

AB - (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.

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

Abstract

ASJC Scopus subject areas

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