Progress towards the total synthesis of communesin B

AEI 75

Jimmy Wu, wujimmy@stanford.edu and Barry M Trost. Department of Chemistry, Stanford University, Stanford, CA 94305
Communesin B is an indoline alkaloid that has been shown to exhibit cytotoxic activity against various different organisms and cell lines. Communesin B possesses a number of intriguing structural features of which include vicinal quaternary stereocenters and two aminal moeties imbedded within a heptacyclic framework. Herein is described two approaches towards the total synthesis of communesin B. The first route utilizes a palladium-catalyzed asymmetric allylation of indole-substituted oxindole derivatives. The second approach takes advantage of a palladium-catalyzed asymmetric C-3 allylation of substituted indoles with allyl alcohol in the presence of 9-BBN.