Abstract
The triply silyl protected 2-methylenecyclohexane-1,3,5-triols 1a-c (C-1: tert-butyldimethylsilyl, TBDMS; C-3:trimethylsilyl, TMS; C-5: tert-butyldiphenylsilyl,TBDPS) were prepared from (R)-(-)-carvonein seven synthetic steps (overall yields: 29-53%).Ozonolysis in the presence
of triethylamine yielded the triply protected2,4,6-trihydroxycyclohexanones 2a-c (85%-quant.). The configurationof the products was proven by NOESY studies and by
chemical correlation.
Key words
alcohols - carbocycles - oxidations - protectinggroups - stereoselective synthesis
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