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A carbohydrate based chiron approach to the lactone intermediate employed in the synthesis of BC-ring fragment of (+)-spirastrellolide A |
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| Authors: | Chao-Chao Wang Yu Tang Ka Yang Xiao-Yu Li Yi-Biao Wu Richard P Hsung |
| Institution: | 1. School of Pharmaceutical Science and Technology, Key Laboratory for Modern Drug Delivery and High-Efficiency, Tianjin University, Tianjin 300072, PR China;2. Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, WI 53705, USA |
| Abstract: | A concise and stereoselective synthesis of the key intermediate used for constructing the BC-ring fragment of (+)-spirastrellolide A is described. The synthetic sequence represents a chiron approach that employs readily available and inexpensive l-arabinose and sets up the stereochemical triad at C20–C22 all from the sugar. This lactone can be used to assemble the spiroketal in the Southern Half through a cyclic acetal-tethered ring-closing metathesis strategy, and is poised for connecting with the Northern Half at C24–C25. |
| Keywords: | Pirastrellolide A Spiroketal containing marine natural product Cyclic acetal-tethered RCM Chiron approach Carbohydrate |
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