Studies of intramolecular Diels-Alder reactions: preparation of methyl spiro[2.4]hepta-4,6-dien-1-yl esters and their internal cycloaddition reactivity

Different routes to the spiro[2.4]hepta-4,6-dien-1-yl esters 5 , 6 , 7 , 26 , and 28 are described and their intramolecular Diels-Alder reactivity examined. A sidechain oxygen substituent is essential for cyclization although its exact role in the cycloaddition remains obscure. The trienes 5 , 6 , a...

Full description

Saved in:
Bibliographic Details
Published in:Canadian journal of chemistry 1984-09, Vol.62 (9), p.1709-1716
Main Authors: Gallacher, Gerard, Ng, Ang Ser, Attah-Poku, Samuel K, Antczak, Kazimierz, Alward, Sandra J, Kingston, John F, Fallis, Alex G
Format: Article
Language:English
Citations: Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Different routes to the spiro[2.4]hepta-4,6-dien-1-yl esters 5 , 6 , 7 , 26 , and 28 are described and their intramolecular Diels-Alder reactivity examined. A sidechain oxygen substituent is essential for cyclization although its exact role in the cycloaddition remains obscure. The trienes 5 , 6 , and 28 cyclize to the tetracyclo[5.4.0 1.7 .0 4.6 .0 6.10 ]undecenes 9 , 10 , and 30 which are useful synthetic intermediates for the preparation of sesquiterpenes.
ISSN:0008-4042
1480-3291
DOI:10.1139/v84-294