Asymmetric synthesis of emericellamide B

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–Wad...

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Bibliographic Details
Published inChinese chemical letters Vol. 26; no. 10; pp. 1209 - 1215
Main Authors Ren, Rong-Guo, Ma, Jing-Yi, Mao, Zhuo-Ya, Liu, Yi-Wen, Wei, Bang-Guo
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier B.V 01.10.2015
Elsevier
Subjects
Antifungal agents
C14
C18
Chemistry
Chemistry, Multidisciplinary
Cyclic depsipeptide
Emericellamide
Macrolactamization
Physical Sciences
Science & Technology
Total synthesis
不对称合成
凝结剂
合成路线
环内酰胺
甲基化
Macrolactamization
Emericellamide
Cyclic depsipeptide
Total synthesis
Antifungal agents
MARINE CYCLIC DEPSIPEPTIDE
REDUCTION
ACIDS
NATURAL-PRODUCTS
DERIVATIVES
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Summary: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.
Bibliography:11-2710/O6
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
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2015.07.023