Cyclopentadecanone 2- cyclododecanone

A cyclopentadecanone (V/74) and a ( )-muscone (V/70) synthesis were carried out by another method related to the reactions discussed in this Chapter. Scheme V/12 shows the thermal transformation of the cyclododecanone derivative, V/71, to V/74 [39], The proposed mechanism for this conversion presumably includes a [1.5] hydrogen shift, followed by a [3.3] sigmatropic rearrangement. 

Microbiological hydroxylation of cyclododecanones and cyclopentadecanones by steroid hydroxylating fungi has been studied attack was fairly non-selective and di-and poly-hydroxylation proceeded readily. Conjugated dienones and diene esters are epoxidized at the y5-double bond by molecular oxygen when heated in solvents which have readily abstractable hydrogens, hence 2,6,6-trimethylcyclohepta-2,4-dienone gave (312). ... 

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