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

William Erb, Jean-Marie Grassot, David Linder, Luc Neuville, Jieping Zhu
Angewandte Chemie 2015 Februrary 3
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.

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