An efficient approach to the asymmetric total synthesis of (-)-anisodine.
-Anisodine (l-6,7-epoxy-3-tropyl-alpha-hydroxytropate), which was isolated from the medicinal plant Scopolia tanguticus Maxim, was the first efficiently prepared using 6-beta-acetyltropine as the starting material via a key step of the Sharpless asymmetric dihydroxylation (AD). The intermediate compounds 10 and 11 showed promising cholinergic activity.
Chang
Junbiao
J
School of Pharmaceuticals, Xinxiang Medical College, China. jbchang@public2.zz.ha.cn
Xie
Weilin
W
Wang
Limin
L
Ma
Nianchun
N
Cheng
Senxiang
S
Xie
Jingxi
J
D000818:Animals; D018680:Cholinergic Antagonists / Q000138:chemical synthesis / Q000737:chemistry; D006168:Guinea Pigs; D006900:Hydroxylation; D007082:Ileum / Q000187:drug effects; D015394:Molecular Structure; D012602:Scopolamine Derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D014326:Tropanes / Q000737:chemistry
D018680:Cholinergic Antagonists; D012602:Scopolamine Derivatives; D014326:Tropanes; C012183:anisodine