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 anhydrous aluminum 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