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Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ6-α-Iodoketone
Authors:Dr Milos Trajkovic  Prof Dr Zorana Ferjancic  Prof Dr Radomir N Saicic  Prof Dr Filip Bihelovic
Institution:Faculty of Chemistry, University of Belgrade, Studentski trg 16, POB 51, 11158 Belgrade 118, Serbia
Abstract:A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama–Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ6- and Δ7-α-iodoketones was developed and applied for the pivotal carbon–carbon bond formation. The scope and limitations of this methodology are also presented.
Keywords:antibiotics  cyclization  natural products  silver  total synthesis
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