Multiselective enzymatic reactions for the synthesis of protected homochiral cis- and trans-1,3,5-cyclohexanetriols |
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| Affiliation: | 1. Pharmaceutical Research Basel-Biological Sciences, F. Hoffmann-La Roche Ltd, Basel, Switzerland;2. Non-clinical Development-Process Research, F. Hoffmann-La Roche Ltd, Basel, Switzerland;1. Department of Food Science and Human Nutrition, Iowa State University, Ames, IA, United States;2. Department of Food Science, Cornell University, Ithaca, NY, United States;1. Dipartimento di Scienze Farmaceutiche (DISFARM), Sezione di Chimica Generale e Organica “Alessandro Marchesini” Università degli Studi di Milano, via Venezian 21, 20133 Milano, Italy;2. Dipartimento di Chimica, Università degli Studi di Milano, via Golgi 19, 20133 Milano, Italy;1. Sorbonne Universités, UPMC Univ Paris 06, CNRS, UMR 8232, IPCM, F-75005 Paris, France;2. PSL, Chimie ParisTech, 11 rue Pierre et Marie Curie, F-75005 Paris, France;3. UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland;1. State Key Laboratory of Advanced Processing and Recycling of Non-ferrous Metal, Lanzhou University of Technology, Lanzhou 730050, PR China;2. Key Laboratory of Nonferrous Metal Alloys and Processing, Ministry of Education, Lanzhou University of Technology, Lanzhou 730050, PR China |
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| Abstract: | 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. |
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