Publication at Faculty of Science, Faculty of Pharmacy in Hradec Králové |
2016
Abstract
The first asymmetric total synthesis of coibacin D, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp., was achieved in six steps starting from simple hept-6-en-1-ol.
The synthetic strategy was based on a chiral Bronsted acid catalyzed enantioselective allylboration and a Ru-carbene complex catalyzed sequential ring-closing and cross-metathesis strategy. The recorded spectro-scopic data and the sign of the optical rotation of the synthesized coibacin D were in agreement with the published data for the isolated compound, which confirmed the proposed structure and absolute configuration.