Recent results in the free radical mediated synthesis of enantiomerically pure,highly functionalized carbocycles from carbohydrates |
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| Institution: | 1. Institute of Chemical Sciences, Department of Organic Chemistry, Faculty of Science, P.J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovak Republic;2. Institute of Pharmacology, Faculty of Medicine, P.J. Šafárik University, SNP 1, 040 66 Košice, Slovak Republic;3. Institute of Physical Chemistry and Chemical Physics, Department of Physical Chemistry, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic;4. Central Laboratories, Slovak University of Technology, Radlinského 9, 812 37 Bratislava, Slovak Republic;1. College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea;2. Department of Bio and Fermentation Convergence Technology, Kookmin University, Seoul 136-702, Republic of Korea;3. Department of Beauty Science, Kwangju Women’s University, Kwangju 506-713, Republic of Korea;4. College of Life Sciences and Biotechnology, Korea University, Seoul 136-701, Republic of Korea;1. National Engineering Research Center for the Emergency Drug, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China;2. State Key Laboratory of Toxicology and Medical Countermeasures, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China;1. Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States;2. Department of Chemistry, Slippery Rock University, Slippery Rock, PA 16057, United States;3. Microbiotix, Inc., Worcester, MA 01605, United States |
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| Abstract: | The free radical cyclization strategy applied to precursors 1, 2 and 14 shows the power and the state of art of this ring closing method for the stereocontrolled synthesis of enantiomerically pure, highly functionalized carbocycles from carbohydrates. The tributyltin hydride mediated free radical cyclization of alkyne tethered N,N-diphenylhydrazones (1) and oxime ethers (2) give the stannylated aminocyclopentitol derivatives 4 and 11, respectively, in moderate yield and with complete stereoselectivity. The 6-exo-trig cyclization of aldehyde/oxime ether 14 derived from D-glucose has been revisited using tributyltin hydride as a reagent. This new protocol shows a superior stereoselection compared with the previous results obtained with samarium diiodide. In summary, an efficient protocol has been set up for the synthesis of enantiomerically pure, polyhydroxy aminocyclohexane derivatives, which are difficult to obtain by other methodologies. |
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