Two-step Synthesis of New γ-Lactones via Cyclization of 7-Chloro-2-(methoxycarbonyl)-4-6-dimethylocta-(2E,4E,6E)-trienoic acid

Jean-Marc Dillenschneider; Laurent Dufossé; Mireille Fouillaud; Nuthathai Sutthiwong; Roger Labia; Alain Valla

Two-step Synthesis of New γ-Lactones via Cyclization of 7-Chloro-2-(methoxycarbonyl)-4-6-dimethylocta-(2E,4E,6E)-trienoic acid

Jean-Marc Dillenschneider ¹ Laurent Dufossé ² Mireille Fouillaud ² Nuthathai Sutthiwong ^{2, 3} Roger Labia ^{4, 1} Alain Valla ^{4, 1}

1 LCSN - Laboratoire de Chimie des Substances Naturelles

2 LCSNSA - Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments

3 TISTR - Thailand Institute of Scientific and Technological Research

4 Chimie et biologie des substances naturelles

Abstract : A new rapid synthesis of γ-lactones, cis fused with a cyclopentenic ring by thermal cyclization of 7-chloro-2-(methoxycarbonyl)-4-6-dimethylocta-7-phenyl (or methyl) (2E,4E,6E)-trienoic acids was reported. The key step implicates an intramolecular cyclization to a cyclopentenyl cation, according to an electrocyclic π2s + π2a conrotatory process, published in a recent paper (from the corresponding diacids). We have investigated the thermal behavior of the corresponding half-esters since; if the cyclization obeys to the proposed mechanism, the diacids, half-esters must also cyclize in a similar manner. Saponification of these led to γ-dilactones via intermediary cyclopropanes. Mechanistic pathways were investigated.

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Journal articles

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Chemical Sciences / Organic chemistry

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Two-step Synthesis of New γ-Lactones via Cyclization of 7-Chloro-2-(methoxycarbonyl)-4-6-dimethylocta-(2E,4E,6E)-trienoic acid

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Two-step Synthesis of New γ-Lactones via Cyclization of 7-Chloro-2-(methoxycarbonyl)-4-6-dimethylocta-(2E,4E,6E)-trienoic acid

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