Synthesis of 2-methyl- and 2-ethylcyclotetradecanones

The Synthesis of Macrocyclic Musks

“…Direct ozonolysis of 91 followed by reduction of the resultant ozonide yields Cetolide (87). 88,89 An ozone-free formation of 87 involves the reaction of 91 with an alkyl nitrite, giving the intermediate oximinocyclopentadecanolide 99; treatment with sodium bisulfite then affords 87. [90][91][92] A one-pot transformation of enol ether 91 to 87, using in situ generated performic acid, has been reported to proceed in 85% yield.…”

“…95 Alternatively, dehydration of 100 over Betonite or phosphoric acid gave 10 which can be readily hydrogenated to 6 (Scheme 31). 96 Electrochemical 97 and Clemmensen 98…”