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

被引：45

作者：

Rinner, U ^{[1
]}

Siengalewicz, P ^{[1
]}

Hudlicky, T ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 01期

关键词：

D O I：

10.1021/ol0169877

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

GRAPHICS 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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页码：115 / 117

页数：3

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