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- W2054928608 abstract "The Formation of Cyclopentadecane-1,5-dione Derivatives by an Oxiranylmethyl Fragmentation. A Synthesis of Muscone A new method for the preparation of cyclopentadecane-1,5-dione (11) and its 3-methylderivative 12, compounds with a musk fragrance, is described. Starting from the readily available bicyclic enones 9 and 10, the epoxy-p-toluenesulfonate 15 and its methylderivatives 20A and 20B were prepared by reduction with diisobutyl-aluminium hydride or sodium borohydride (to 13 and 18A, 18B), epoxidation with m-chloroperbenzoic acid (to 14 and 19A, 19B), followed by tosylation. Heating of 15 and 20A or 20B with calcium carbonate in water/dioxane under reflux caused fragmentation leading to the diketones 11 and 12 in high yields. The same fragmentation also occurred with sodium hydrogencarbonate in dimethylsulfoxide at 160°, but in lower yields. The conversion of 12 into rac-muscone (2) was accomplished by developing a method for selectively forming the monotosylhydrazone 27. The latter was reduced with sodium borohydride and the crude alcohol 28 oxidized to 2. Unexpectedly the pyrolysis of the epoxy-acetate 29 at 350° in a sealed glass tube led to the bicyclic ketone 10. Treatment of 3-methylcyclopentadecane-1,5-dione (12) with peracetic acid and boron trifluoride etherate gave the stable crystalline ozonide 33." @default.
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- W2054928608 date "1977-09-21" @default.
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- W2054928608 title "Oxiranylmethyl-Fragmentierung zur Bildung von Cyclopentadecan-1,5-dion-Derivaten. Eine Musconsynthese" @default.
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- W2054928608 doi "https://doi.org/10.1002/hlca.19770600618" @default.
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