TANDEM INTRAMOLECULAR DIELS-ALDER (TIMDA) REACTIONS - BRANCHED SUBSTRATE STUDIES AND NEW SYNTHETIC PATHWAYS

被引：8

作者：

BRODNEY, MA ^{[1
]}

OLEARY, JP ^{[1
]}

HANSEN, JA ^{[1
]}

GIGUERE, RJ ^{[1
]}

机构：

[1] SKIDMORE COLL,DEPT CHEM,SARATOGA SPRINGS,NY 12866

来源：

SYNTHETIC COMMUNICATIONS | 1995年 / 25卷 / 04期

关键词：

D O I：

10.1080/00397919508011386

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using a malonic ester route, the first branched tandem intramolecular Diels-Alder (TIMDA) precursor, 3, was synthesized from sorbic acid in seven steps (15% overall yield). Treatment with Lewis acid catalysts (e.g., boron trifluoride etherate) affects the TIMDA reaction to afford a new fused-tetracyclic, 4, as two diastereomers (1:1). An alternative synthetic route to key intermediates used in the synthesis of linear TIMDA precursors has also been achieved.

引用

页码：521 / 531

页数：11

共 8 条

[1]

COREY EJ, 1972, TETRAHEDRON LETT, V12, P3769

[2] A CONVENIENT METHOD FOR THE PREPARATION OF N-METHOXYAMIDES [J].