Isolation and structure elucidation of topsentin (1) and bromotopsentin (2) are described. These novel indole alkaloids have been shown to have antitumor and antiviral activities. Their structures were determined on the basis of spectral data, and bromotopsentin was correlated structurally with topsentin by catalytic debromination. Syntheses of 1 and several analogues are also reported.
This document is the accepted manuscript version of a published work that appeared in final form in The Journal of Organic Chemistry after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/jo00258a009. This article may be cited as: Tsujii, S., Rinehart, K. L., Gunasekera, S. P., Kashman, Y., Cross, S. S., Lui, M. S., Pomponi, S. A., & Diaz, M. C. (1988). Topsentin, bromotopsentin, and dihydrodeoxybromotopsentin; antiviral and antitumor bis(indolyl)imidazoles from Caribbean deep-sea sponges of the family Halichondriidae. Structural and synthetic studies. The Journal of Organic Chemistry, 53(23), 5446-5453. doi:10.1021/jo00258a009
Florida Atlantic University. Harbor Branch Oceanographic Institute contribution #670.