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Journal articles
Two-step Synthesis of New γ-Lactones via Cyclization of 7-Chloro-2-(methoxycarbonyl)-4-6-dimethylocta-(2E,4E,6E)-trienoic acid
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.
Cited literature [4 references]
https://hal.univ-reunion.fr/hal-01188091
Contributor : Claire Tessier <>
Submitted on : Saturday, November 19, 2016 - 8:48:11 AM
Last modification on : Monday, July 20, 2020 - 10:09:43 AM
Long-term archiving on: : Monday, March 27, 2017 - 9:06:08 AM
Contributor : Claire Tessier <>
Submitted on : Saturday, November 19, 2016 - 8:48:11 AM
Last modification on : Monday, July 20, 2020 - 10:09:43 AM
Long-term archiving on: : Monday, March 27, 2017 - 9:06:08 AM
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Dillenschneider2016B_hal.pdf
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