A new method for the construction of the hydroxylated tropane skeleton: enantioselective synthesis of (-)-Bao Gong Teng A.
An efficient and highly diastereoselective method for the construction of the hydroxylated tropane skeleton is described. The method features a new intramolecular reductive coupling reaction of N-acyl N,O-acetal with aldehyde, cooperatively mediated by BF(3)·OEt(2) and SmI(2). On the basis of this method, a new enantioselective total synthesis of (-)-Bao Gong Teng A has been accomplished.
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, P. R. China.
Geng-Jie
GJ
Lin
Xiao
X
Zheng
Pei-Qiang
PQ
Huang
D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014326:Tropanes / Q000138:chemical synthesis* / Q000737:chemistry*
D014326:Tropanes; C027863:bao gong teng A