Author/Authors :
Li, Hao NankaiUniversity - Research Institute of Elemento-Organic Chemistry - State Key Laboratory of Elemento-Organic Chemistry, China , Hu, Tianshun Nankai University - Research Institute of Elemento-Organic Chemistry - State Key Laboratory of Elemento-Organic Chemistry, China , Wang, Kailiang Nankai University - Research Institute of Elemento-Organic Chemistry - State Key Laboratory of Elemento-Organic Chemistry, China , Liu, Yuxiu Nankai University - Research Institute of Elemento-Organic Chemistry - State Key Laboratory of Elemento-Organic Chemistry, China , Fan, Zhijin Nankai University - Research Institute of Elemento-Organic Chemistry - State Key Laboratory of Elemento-Organic Chemistry, China , Huang, Runqiu Nankai University - Research Institute of Elemento-Organic Chemistry - State Key Laboratory of Elemento-Organic Chemistry, China , Wang, Qingmin Nankai University - Research Institute of Elemento-Organic Chemistry - State Key Laboratory of Elemento-Organic Chemistry, China
Abstract :
The first total synthesis of (+)-deoxytylophorinine has been accomplished in 6 linear steps and with 39.6% overall yield. An important feature of this synthesis is that Friedel-Craft acylation of (S)-1-benzyloxycarbonylpyrrolidine-2-acetyl chloride with phenylmethylether catalyzed with fresh anhydrousaluminum chloride to provide 2-(4-methoxyphenacyl)pyrrolidine and cleavage of the Cbz group have been proceeded in one pot. We have found that (+)-deoxytylophorinine shows excellent anti-TMV activity.
Keywords :
Phenanthroindolizidine alkaloids , (+) , deoxytylophorinine , total synthesis , antiviral activity , tobacco mosaic virus
