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

…, SK Attah-Poku, K Antczak, SJ Alward…

Index: Gallacher, Gerard; Ng, Ang Ser; Attah-Poku, Samuel K.; Antczak, Kazimierz; Alward, Sandra J.; et al. Canadian Journal of Chemistry, 1984 , vol. 62, p. 1709 - 1716

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Citation Number: 14

Abstract

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. 01.7. 04.6. 06.10] undecenes 9, 10, and 30 which are useful synthetic intermediates for the preparation of sesquiterpenes.