Type 2 intramolecular N-acylnitroso Diels-Alder reaction:: Scope and application to the synthesis of medium ring lactams

被引：37

作者：

Sparks, SM ^{[1
]}

Chow, CP ^{[1
]}

Zhu, L ^{[1
]}

Shea, KJ ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 09期

关键词：

D O I：

10.1021/jo049897z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Heteroatom variants of the type 2 intramolecular Diels-Alder reaction provide an efficient method for the preparation of bridged bicyclic heterocycles. The type 2 variant of the intramolecular N-acylnitroso Diels-Alder reaction is an effective method for the synthesis of bridged bicyclic oxazinolactams. Structural studies of the cycloadducts have allowed for quantification of the deformations of the bridgehead functionalities and provided a strategy for the stereoselective synthesis of substituted seven- and eight-membered ring lactams. Diastereoselective cycloadditions followed by cleavage of the oxazine ring afford azepin-2-ones or azocin-2-ones.

引用

页码：3025 / 3035

页数：11

共 74 条

[1] First total synthesis of the marine alkaloids (±)-fasicularin and (±)-lepadiformine based on stereocontrolled intramolecular acylnitroso-Diels-Alder reaction [J].