Total synthesis and morphogenesis-inducing activity of (±)-thallusin and its analogues

Total synthesis of (+/-)-thallusin was achieved using Hg(OTf)(2)-PhNMe2-induced olefin cyclization, and Suzuki coupling with a pyridyllboronic acid derivative. Hg(OTf)(2) also acted as a catalyst to isomerize the double bond into the more thermodynamically stable isomer when treated in toluene. Synthetic (+/-)-thallusin as well as an analogue showed morphogenesis-inducing activity. (c) 2007 Elsevier Ltd. All rights reserved.