Enantioselective synthesis of putative lipiarmycin aglycon related to fidaxomicin/tiacumicin B. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2015

Enantioselective synthesis of putative lipiarmycin aglycon related to fidaxomicin/tiacumicin B.

Résumé

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.

Domaines

Chimie
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Dates et versions

hal-01138237 , version 1 (01-04-2015)

Identifiants

  • HAL Id : hal-01138237 , version 1
  • PUBMED : 25422174

Citer

William Erb, Jean-Marie Grassot, David Linder, Luc Neuville, Jieping Zhu. Enantioselective synthesis of putative lipiarmycin aglycon related to fidaxomicin/tiacumicin B.. Angewandte Chemie International Edition, 2015, 54 (6), pp.1929-1932. ⟨hal-01138237⟩
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