79801-33-5

Upstream product

• 2065-66-9 methyl-triphenylphosphonium iodide 
• 121401-44-3 (2-trimethylsilyloxy-3-cyclohexen-1-yl)-ethanone 
• 121952-94-1 (E)-7-Methyl-octa-2,6-dienoyl chloride 
• 764-32-9 5-methyl-4-hexenal 
• 88197-02-8 (E)-7-methyl-octa-2,6-dienoic acid 

Downstream Products

• 121401-22-7 3-(methoxymethoxy)methyl-4-(1-methylethenyl)-2-cyclohexenone 
• 121401-57-8 ((1S,4S,5R)-5-Isopropenyl-4-methoxymethoxymethyl-2-oxo-4-vinyl-cyclohexyl)-acetic acid methyl ester 
• 121429-34-3 ((1S,2S,4S,5R)-2-Hydroxy-5-isopropenyl-4-methoxymethoxymethyl-4-vinyl-cyclohexyl)-acetic acid methyl ester 
• 121401-23-8 (3α,4β)-3-ethenyl-3-(methoxymethoxy)methyl-4-(1-methylethenyl)-cyclohexanone 

Relevant academic research and scientific papers

Type III Intramolecular Cycloadditions of Vinylketenes

Treatment of trans α,β-unsaturated acid chlorides with Et3N in benzene at reflux gives a ca. 1:1 mixture of cis and trans α,β-unsaturated ketenes in excellent yield.If there is a second double bond in the side chain, the cis isomer undergoes a type III intramolecular cycloaddition to produce a bicyclohept-3-en-6-one and/or a bicyclohept-2-en-6-one in 30-50percent yield from the acid chloride.The effect of substituents on the stereochemistry and regiochemistry of the cycloaddition is described.

TOTAL SYNTHESIS OF VARIOUS ELEMANOLIDES

Starting with a suitable substituted divinyl cyclohexanone, eleven naturally occurring 12.8-elemanolides bearing exo-methylene or methyl groups at C-11 and differing in substitution as well as in relative configuration, have been synthesized in racemic form.An approach to elemanolides with additional oxygen functionalities is principally possible by modification of the basic concept.Methods for the oxidative generation of terpenoid exo-methylene lactone and furan units are exemplified by synthesis of menthofuran and the p-menthenolides from isopulegols.