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Enantioselective Synthesis of Putative Lipiarmycin Aglycon Related to Fidaxomicin/Tiacumicin B |
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| Authors: | Dr William Erb Dr Jean‐Marie Grassot Dr David Linder Dr Luc Neuville Prof?Dr Jieping Zhu |
| Institution: | 1. Centre de Recherche de Gif, Laboratoire International Associé, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif‐sur‐Yvette Cedex (France);2. Laboratory of Synthesis and Natural Products, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL‐SB‐ISIC‐LSPN, BCH 5304, 1015 Lausanne (Switzerland) http://lspn.epfl.ch |
| Abstract: | An enantioselective synthesis of a putative lipiarmycin aglycon was accomplished and features: 1) Brown′s enantioselective alkoxyallylboration and allylation of aldehydes, 2) chain elongation by iterative Horner–Wadsworth–Emmons olefination, 3) Evans’ aldol reaction and 4) an ene‐diene ring‐closing metathesis. A neighboring‐group‐assisted chemoselective reductive desilylation was uncovered in this study and was instrumental to the realization of the present synthesis. |
| Keywords: | macrocycles metathesis natural products protecting groups total synthesis |