Further studies on CAB approach toward chemical conversion of C19-diterpenoid alkaloids to taxoids: synthesis of the vital intermediate C-nor-aconanone

被引：2

作者：

Shen, Xiang-Li ^{[1
,2
]}

Chen, Qiao-Hong ^{[1
]}

Wang, Feng-Peng ^{[1
]}

机构：

[1] Sichuan Univ, W China Coll Pharm, Dept Chem Med Nat Prod, Chengdu 610041, Peoples R China

[2] Sichuan Univ, W China Univ Hosp 2, Chengdu 610041, Peoples R China

来源：

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH | 2009年 / 11卷 / 02期

基金：

中国国家自然科学基金;

关键词：

N; 19-seco-C19-diterpenoid alkaloid; 17-seco-C19-diterpenoid alkaloid; Aconane-type diterpene; semipinacol rearrangement; imine; m-CPBA-LTA oxidation; NORDITERPENOID ALKALOIDS; ACETYLLYCOCTONINE; REARRANGEMENT; DERIVATIVES; OXIDATION; PRODUCTS; ACCESS;

D O I：

10.1080/10286020801967128

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

In the title study, the synthesis of the vital intermediate C-nor-aconanone (3) from 4 was completed through 11 steps, mainly including semipinacol rearrangement, formation of the imines by the treatment of 10 or 20 with NBS, the cleavage of N-C(19) bonds in 11 or 21 by treatment with m-CPBA and subsequently with LTA, as well as the rupture of the N-C(17) bonds in 22 by a modified Nef reaction (NaH/t-BuOHKMnO4/H2O). One-pot procedure was successfully developed starting from 11 or 21 to afford the N,19-seco-C-nor product 15 or 22, respectively, in reasonably good yields.

引用

页码：97 / 109

页数：13