Total synthesis of cyclodepsipeptide Hikiamides A-C
10.11665/j.issn.1000-5048.20180207
- VernacularTitle:天然环酯肽Hikiamides A-C的全合成
- Author:
Donglin FU
1
;
Xuemin RAO
;
Jinyi XU
;
Weijia XIE
;
Xiaoming WU
Author Information
1. 中国药科大学药物科学研究院
- Publication Type:Journal Article
- Keywords:
Fusarium sp.;
cyclodepsipeptide;
Hikiamides A-C;
PPARγ;
natural products;
total synthesis
- From:
Journal of China Pharmaceutical University
2018;49(2):181-186
- CountryChina
- Language:Chinese
-
Abstract:
Total synthesis of cyclodepsipeptide Hikiamides A-C was described. Fragment convergent condensation method was applied for the preparation of Hikiamides A-C, starting from Commercially available amino acid such as L-N-Boc-Phe-OH, L-N-Boc-Trp-OH, L-N-Cbz-Van-OH etc. Tripeptide fragments(compounds 5a/5b)and dipeptide fragments(compounds 8a/8b)were first prepared. The subsequent condensation of the resulted two fragments provided protected linear pentapetides(compounds 9a/9b/9c); Finally, the linear pentapetide was cyclized by a mixed condensing agents comprised of PyBOP and HBTU. Hikiamides A-C was obtained with total yields of 9%, 11% and 6. 5%, respectively. Compared with the natural source, this method has the advantages of low cost, convenient operation and high yield, which effectively solves the problem of low isolated yield of Hikiamides A-C from Fusarium sp.
