Synthesis of cis-jasmone and other cis-rethrones
Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690001024
Abstract
Convenient three-stage syntheses (32–35% overall) of cis-jasmone and cis-cinerone, from readily available 3-(5-methyl-2-furyl)propionaldehyde (2) are described. Witting reactions, under' salt-free conditions are used for the cis-alkenylation (ca 12%trans is concurrently produced). Use of an allyl Witting reagent (3c) led to a mixture (2:3) of cis-and trans-dienes which was converted into a mixture of cis-and trans-pyrethrone, from which cis-pyrethrone was separated and characterised. Thermal rearrangement of cis-pyrethrone gavi isopyrethrone.
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Journal Name：Journal of the Chemical Society C: Organic
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CAS no.: 89640-58-4
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