Enantioselective Total Synthesis of (-)-Deoxoapodine.
作者： Taek Kang , Kolby L. White , Tyler J. Mann , Amir H. Hoveyda , Mohammad Movassaghi
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摘要: The first enantioselective total synthesis of (-)-deoxoapodine is described. Our this hexacyclic aspidosperma alkaloid includes an efficient molybdenum-catalyzed ring-closing metathesis reaction for desymmetrization advanced intermediate and to introduce the C5-quaternary stereocenter. After C21-oxygenation, pentacyclic core was accessed via electrophilic C19-amide activation transannular spirocyclization. A biogenetically inspired dehydrative C6-etherification proved highly effective secure F-ring fourth contiguous stereocenter with complete stereochemical control.
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