Synthesis of the heterocyclic core of the alkaloids martinelline and martinellic acid

被引：51

作者：

Hadden, M ^{[1
]}

Nieuwenhuyzen, M ^{[1
]}

Osborne, D ^{[1
]}

Stevenson, PJ ^{[1
]}

Thompson, N ^{[1
]}

机构：

[1] Queens Univ Belfast, Sch Chem, Belfast BT9 5AG, Antrim, North Ireland

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 36期

关键词：

martinelline; martinellic acid; imino Diels-Alder; alkaloid;

D O I：

10.1016/S0040-4039(01)01267-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tricyclic core of martinelline and martinellic acid was rapidly assembled utilising an imino Diels-Alder reaction of an imine derived from cinnamaldehyde with a cyclic enamide. The cycloaddition was completely regioselective though the exo endo selectivity was poor. These diastercoisomers were readily separated by flash chromatography and the relative stereochemistry of the exo-isomer confirmed by single crystal X-ray crystallography. This intermediate was converted to the central core of the aforementioned alkaloids in five additional synthetic operations. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6417 / 6419

页数：3

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