- Multiselective enzymatic reactions for the synthesis of protected homochiral cis- and trans-1,3,5-cyclohexanetriols
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For the synthesis of the potentially antipsoriatic vitamin D derivative 3 (Ro 65-2299) an efficient and multiselective enzymatic step had been developed in which the easily accessible trans-1,3,5-triacetoxy-cyclohexane 5 was selectively monohydrolyzed in the presence of the cis-isomer 8 to give (1R,3R)-1,3-diacetoxy-5-hydroxy-cyclohexane 6 in high enantiomeric excess (>99%) and yield (84%). Furthermore, for the synthesis of the enantiomer of 3, a simple and efficient enzymatic procedure for the asymmetric acetylation of cis-1,5-dihydroxy-3-(tert-butyldimethylsilanoxy)-cyclohexane 10 in an anhydrous organic solvent providing (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanoxy)-cyclohexane 11 in >99% ee and quantitative yield is described. Copyright (C) 2000 Elsevier Science Ltd.
- Wirz, Beat,Iding, Hans,Hilpert, Hans
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- A Novel Synthesis of 19-Nor 1α,25-dihydroxyvitamin D3 and Related Analogues
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19-Nor-1α,25-dihydroxyvitamin D3 (2) was synthesized from A-ring precursor 5 and ketone 4.Two synthesis of 5 were studied; one starting from (-)-quinic acid as a template and one starting from cis-1,3,5-cyclohexanetriol via a chemoenzymatic approach.
- Huang, Pei-qiang,Sabbe, Katrien,Pottie, Mieke,Vandewalle, Maurits
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p. 8299 - 8302
(2007/10/02)
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