Total synthesis of chrysamide B

被引：9
|
作者：
Berube, Christopher [1 ]
Carpentier, Claudia [1 ]
Voyer, Normand [1 ]
机构：
[1] Univ Laval, PROTEO, Dept Chim, Fac Sci & Genie, 1045 Ave Med, Quebec City, PQ G1V 0A6, Canada
来源：
TETRAHEDRON LETTERS | 2017年 / 58卷 / 24期
基金：
加拿大自然科学与工程研究理事会;
关键词：
Chrysamide; Chiral piperazines; Nitro natural products; Chiral epoxides; Natural product synthesis; POLYMER-BOUND OXIME; ASYMMETRIC EPOXIDATION; DRAGMACIDIN-B; A-C; PIPERAZINE; DERIVATIVES; OXIDATION; PEPTIDES; ANALOGS;
D O I：
10.1016/j.tetlet.2017.04.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We report an efficient synthesis of the dimeric trans-epoxyamide chrysamide B, recently isolated from the deep-sea-derived fungus Penicillium chrysogenum SCSI041001. Our synthetic strategy exploits a convergent approach using solid,phase peptide synthesis for the piperazine core and a Sharpless-Katsuki epoxidation to prepare the chiral epoxyacid. The double amidation final step provides chrysamide B that was thoroughly characterized with all spectra identical to those of the natural sample. The approach was devised to facilitate the preparation of a library of analogs of chrysamide B. (C) 2017 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2334 / 2336
页数：3
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