Synthesis and formation mechanism of ocotillol and its epimer
10.11665/j.issn.1000-5048.20160305
- VernacularTitle:Ocotillol及其差向异构体的合成与形成机制
- Author:
Wenzhi WANG
1
;
Yangrong XU
;
Xinli LI
;
Jingjing YANG
;
Qingguo MENG
Author Information
1. 烟台大学新型制剂与生物技术药物研究山东省高校协同创新中心；分子药理和药物评价教育部重点实验室
- Publication Type:Journal Article
- Keywords:
ocotillol;
epimer;
synthesis;
formation mechanism
- From:
Journal of China Pharmaceutical University
2016;47(3):282-287
- CountryChina
- Language:Chinese
-
Abstract:
Ocotillol(3)and its epimer(4)have been synthesized from 20(S)-protopanaxatriol ［20(S)-PPT］ via two routes, and their formation mechanism has been speculated. Route 1: Compounds 3 and 4 were obtained from 20(S)-PPT by oxidation with m-CPBA at the yield of 44. 1% and 28. 6%, respectively. Route 2: Compounds 3 and 4 were prepared from 20(S)-PPT by acetylation, oxidation and saponification at the yield of 16. 4% and 16. 2%, respectively. The formation mechanism of compounds 3 and 4 is speculated as below: 1)The chemical environments of both sides of C24(25)double bond in 20(S)-PPT are different due to the existence of intramolecular hydrogen bond, which led to the different oxidation ratio of the two sides, and the different yields of compounds 3 and 4. 2)There is not intramolecular hydrogen bond in acetylated 20(S)-PPT, and the chemical environments of both sides of C24(25)double bond are similar, which resulted in almost equal yields of compounds 3 and 4 synthesized through oxidation with m-CPBA, intramolecular SN2 and saponification.
