The Imidato-Alkenyllithium Route for the Synthesis of the Isoquinocycline-Pyrrolopyrrole Substructure

被引：10

作者：

Breuning, M. Andre ^{[1
]}

Harms, Klaus ^{[1
]}

Koert, Ulrich ^{[1
]}

机构：

[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 06期

关键词：

QUINOCYCLINE COMPLEX; RADICALS; SUGAR;

D O I：

10.1021/ol200085g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convergent and effective synthesis of the pyrrolopyrrole substructure (CDEFG) of the Isoquinocyclines Is reported. A key step is a tin lithium exchange of an imidato-alkenyltin compound (a ring G equivalent) and the subsequent acylation with a lactone. The resulting acetal is used successfully for the ring F closure to the pyrrolopyrrole. The sole formation of the isoquinocycline N,O-acetal epimer is in accordance with the proposed mechanism for the isomerization of quinocyclines to isoquinocyclines.

引用

页码：1402 / 1405

页数：4

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