Model studies for the synthesis of the marine hepatotoxin cylindrospermopsin. Preparation of a bicyclic guanidine with the hydroxymethyluracil side chain.

被引：25

作者：

Snider, BB ^{[1
]}

Xie, CY ^{[1
]}

机构：

[1] Brandeis Univ, Dept Chem, Waltham, MA 02254 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 39期

基金：

美国国家卫生研究院;

关键词：

guanidines; pyrimidines; substitution;

D O I：

10.1016/S0040-4039(98)01470-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ketone 13 was prepared by coupling acetylene 7b with aldehyde 9 in a convergent six-step sequence. In the key step, hydrogenation of bromo ketone 14 afforded 81% of an 81:14:4.5:0.5 mixture of 15-18. Hydrolysis of the major product 15 in concentrated hydrochloric acid at reflux afforded cylindrospermopsin model 5 in 95% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

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收藏

页码：7021 / 7024

页数：4

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