Enantioselective Synthesis of Putative Lipiarmycin Aglycon Related to Fidaxomicin/Tiacumicin B

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 enediene 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.


Published in:
Angewandte Chemie International Edition, 54, 6, 1929-1932
Year:
2015
Publisher:
Wiley-Blackwell
ISSN:
1433-7851
Keywords:
Laboratories:




 Record created 2015-02-02, last modified 2018-09-13


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