Citation: Rong-Guo Ren, Jing-Yi Ma, Zhuo-Ya Mao, Yi-Wen Liu, Bang-Guo Wei. Asymmetric synthesis of emericellamide B[J]. Chinese Chemical Letters, ;2015, 26(10): 1209-1215. doi: 10.1016/j.cclet.2015.07.023 shu

Asymmetric synthesis of emericellamide B

1.
1 Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, Shanghai 200433, China;
2.
2 School of Pharmacy, Fudan University, Shanghai 200433, China

Corresponding author: Bang-Guo Wei,
Received Date: 23 June 2015
Available Online: 14 July 2015
Fund Project: We thank the National Natural Science Foundation of China (Nos. 21472022, 21272041, 21072034) (Nos. 21472022, 21272041, 21072034)

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.
- Cyclic depsipeptide,
- Antifungal agents,
- Emericellamide,
- Total synthesis,
- Macrolactamization
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