Asymmetric synthesis of emericellamide B

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Asymmetric synthesis of emericellamide B

Rong-Guo Ren , Jing-Yi Ma , Zhuo-Ya Mao , Yi-Wen Liu , Bang-Guo Wei

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

shu

Asymmetric synthesis of emericellamide B

通讯作者: Bang-Guo Wei,

基金项目:
We thank the National Natural Science Foundation of China (Nos. 21472022, 21272041, 21072034) (Nos. 21472022, 21272041, 21072034)

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.

关键词:

English

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: 29 July 2015
Fund Project:

Abstract: 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.

Key words:

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