The structure and synthesis of tsitsikammafuran:: A new furanosesquiterpene from a South African Dysidea sponge

被引：53

作者：

McPhail, KL ^{[1
]}

Rivett, DEA ^{[1
]}

Lack, DE ^{[1
]}

Davies-Coleman, MT ^{[1
]}

机构：

[1] Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa

来源：

TETRAHEDRON | 2000年 / 56卷 / 47期

基金：

新加坡国家研究基金会;

关键词：

marine metabolites; furan; sesquiterpene; aryl halides;

D O I：

10.1016/S0040-4020(00)00910-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three furanosesquiterpenes. the new tsitsikammafuran (1) and the known nakafurans-8 (2) and -9 (3) were isolated from a South African Dysidea sponge. The structure of tsitsikammafuran, initially proposed as 3-[(furan-3-yl)methyl]-p-cymene, from a combination of biosynthetic arguments and the available spectroscopic data, was unequivocally confirmed by the synthesis of 1 from thymol. The synthesis of two regioisomers of tsitsikammafuran, 4-[(furan-3-yl)methyl]-m-cymene (4) and 2-[(furan-3-yl)methyl]-p-cymene (22), from p-cresol and 2-bromo-2-nitrocamphane respectively, further supported the structural assignment of 1. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9391 / 9396

页数：6

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