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Synthesis 2003(12): 1827-1836
DOI: 10.1055/s-2003-41025
DOI: 10.1055/s-2003-41025
PAPER
© Georg ThiemeVerlag Stuttgart · New York
Stereoselective Synthesis ofEnantiomerically Pure, Orthogonally Protected 2-Methylenecyclohexane-1,3,5-triolsand 2,4,6-Trihydroxycyclohexanones
Weitere Informationen
Received
4 July 2003
Publikationsdatum:
13. August 2003 (online)
Publikationsverlauf
Publikationsdatum:
13. August 2003 (online)
![](https://www.thieme-connect.de/media/synthesis/200312/lookinside/thumbnails/10.1055-s-2003-41025-1.jpg)
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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