Total synthesis of sauropunol A-D isolated from Sauropus rostratus genus plants
10.11665/j.issn.1000-5048.20170407
- VernacularTitle:龙脷叶中天然产物sauropunol A-D的全合成
- Author:
Zihao WANG
;
Chengqian WANG
;
Jinyi XU
;
Xiaoming WU
;
Weijia XIE
- Keywords:
Sauropus rostratus;
sauropunol A-D;
3,6-anhydrohexosides;
intramolecular cyclization;
natural products;
total synthesis
- From:
Journal of China Pharmaceutical University
2017;48(4):432-439
- CountryChina
- Language:Chinese
-
Abstract:
Sauropunol A-D potentially with anti-inflammatory,anti-bacterial activities were recently isolated from traditional Chinese medicinal plant Sauropus rostratus.Herein,we report the total synthesis of sauropunol (A-D) starting from a commercially available 2-deoxy-D-arabino-hexopyranose.The trifluoromethane sulfonation of intermediates could simultaneously trigger intramolecular cyclization to afford 3,6-anhydro hexofuranoside scaffold.The following deprotection reaction could produce sauropunol A,B and C/D with total yields of 21％,5％,and 17％ (isomer sauropunol C/D),respectively.Structures of the target compounds were confirmed by comparison with NMR spectroscopic properties of those previously reported.
