Transannular Diels-Alder model studies on the total synthesis of chatancin.: The furanophane approach.: Part 1:: Assembly of the acyclic substrates

被引：13

作者：

Toró, A ^{[1
]}

Wang, Y ^{[1
]}

Deslongchamps, P ^{[1
]}

机构：

[1] Univ Sherbrooke, Inst Pharmacol Sherbrooke, Lab Synthese Organ, Sherbrooke, PQ J1H 5N4, Canada

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 14期

基金：

加拿大自然科学与工程研究理事会;

关键词：

dithianes; furans; lithiations; macrocycles;

D O I：

10.1016/S0040-4039(99)00323-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of three generations of model substrates with advancing similarity to chatancin are presented. In the first two generations, an Ireland-Claisen based six-step sequence supplied the trans-dienophile to be connected by dithiane chemistry to furfurals. In the third generation, a homogeraniol based dienophile aldehyde was coupled with a dilithiated 3-furoic acid. Subsequently, all three generations were concluded with similar functional group modifications as a preparation for a malonate-furyl chloride based macrocyclization. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：2765 / 2768

页数：4

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