Asymmetric synthesis of emericellamide B  

Asymmetric synthesis of emericellamide B

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作  者:Rong-Guo Ren Jing-Yi Ma Zhuo-Ya Mao Yi-Wen Liu Bang-Guo Wei 

机构地区:[1]Department of Chemistry and Institutes of Biomedical Sciences, Fudan University [2]School of Pharmacy, Fudan University

出  处:《Chinese Chemical Letters》2015年第10期1209-1215,共7页中国化学快报(英文版)

基  金:the National Natural Science Foundation of China (Nos. 21472022, 21272041, 21072034);Key Laboratory for Chemical Biology of Fujian Province for financial support

摘  要:Asymmetric total synthesis of emericellamide B(9.4%, 17 longest linear steps) is detailed in this report. In this synthetic route, the highly methylated(2R,3R,4S,6S)-3-hydroxy-2,4,6-trimethyldodecanoic acid(HTMD) unit was effectively prepared through the asymmetric methylation, Wittig and Horner–Wadsworth–Emmons reaction. Moreover, pentafluorophenyl diphenylphophinate(FDPP) proved to be an effective condensation reagent for the macrolactamization between C14 and C18.Asymmetric total synthesis of emericellamide B(9.4%, 17 longest linear steps) is detailed in this report. In this synthetic route, the highly methylated(2R,3R,4S,6S)-3-hydroxy-2,4,6-trimethyldodecanoic acid(HTMD) unit was effectively prepared through the asymmetric methylation, Wittig and Horner–Wadsworth–Emmons reaction. Moreover, pentafluorophenyl diphenylphophinate(FDPP) proved to be an effective condensation reagent for the macrolactamization between C14 and C18.

关 键 词:Cyclic depsipeptide Antifungal agents Emericellamide Total synthesis Macrolactamization 

分 类 号:O621.3[理学—有机化学]

 

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