REVISED STRUCTURE AND CONVERGENT SYNTHESIS OF NEMERTELLINE, THE NEUROTOXIC QUATERPYRIDINE ISOLATED FROM THE HOPLONEMERTINE SEA WORM

被引：31

作者：

CRUSKIE, MP ^{[1
]}

ZOLTEWICZ, JA ^{[1
]}

ABBOUD, KA ^{[1
]}

机构：

[1] UNIV FLORIDA,DEPT CHEM,GAINESVILLE,FL 32611

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 23期

关键词：

D O I：

10.1021/jo00128a021

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The correct structure of the quaterpyridine nemertelline first isolated from hoplonemertine sea worms has been identified as 2 (3,2':3',4 '':2 '',3triple prime-quaterpyridine). The natural product was synthesized using palladium(0)-catalyzed cross-coupling of 3-(tributylstannyl)-2,3'-bipyridine (3) and 4-chloro-2,3'-bipyridine (4). The bipyridines were prepared in the presence of the Pd catalyst by cross-coupling 2-bromo-3-(tributylstannyl)pyridine (5) and 2,4-dichloropyridine with 3-diethyl(pyridyl)borane, respectively. X-ray analysis confirmed the structure of 2 and provided its conformation in the solid state. The proton NMR spectrum of 2 identifies it as the natural product first reported in 1976.

引用

页码：7491 / 7495

页数：5

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