- Stereoselective synthesis of enantiomerically pure, orthogonally protected 2-methylenecyclohexane-1,3,5-triols and 2,4,6-trihydroxycyclohexanones
-
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)-(-)-carvone in seven synthetic steps (overall yields: 29-53%). Ozonolysis in the presence of triethylamine yielded the triply protected 2,4,6-trihydroxycyclohexanones 2a-c (85%-quant.). The configuration of the products was proven by NOESY studies and by chemical correlation.
- Kirsch, Stefan,Bach, Thorsten
-
p. 1827 - 1836
(2007/10/03)
-
- A novel and enantioselective approach to the synthesis of cyclohexane carbocyclic nucleosides starting from (-)-carvone
-
3,5-dihydroxy-4-(hydroxymethyl)-1-cyclohexanyl adenine has been synthesized starting from (-)-carvone. The adenine base was introduced via Mitsunobu reaction. Conformational analysis showed that the base still adopts the equatorial position at the expense of three axial substituents.
- Wang, Jing,Herdewijn, Piet
-
p. 591 - 592
(2007/10/03)
-
- Enantioselective approach to the synthesis of cyclohexane carbocyclic nucleosides
-
(R)-(-)-Carvone was used as starting material for the synthesis of a new series of 2-(hydroxymethyl)-cyclohexane-1,3-diol nucleosides. The enantioselective precursors of the nucleoside analogues were obtained via a stereo- and regioselective hydroboration reaction. The compounds have equatorial oriented base moieties despite the presence of three other axial substituents.
- Wang, Jing,Busson, Roger,Blaton, Norbert,Rozenski, Jef,Herdewijn, Piet
-
p. 3051 - 3058
(2007/10/03)
-
- Efficient Enantiospecific Synthesis of Key A-Ring Synthons for the Preparation of 1α,25-Dihydroxyvitamin D3 Using a Chromium((II)-Mediated Reaction
-
Key A-ring synthons for the synthesis of 1α,25-dihydroxyvitamin D3 have been prepared efficiently from (R)-(-)-carvone by use of diastereoselective chromium(II)-mediated addition of an allylic halide to an aldehyde as a key step.
- Hatakeyama, Susumi,Numata, Hirotoshi,Osanai, Ken,Takano, Seiichi
-
p. 3515 - 3517
(2007/10/02)
-