Indexed on: 13 Oct '07Published on: 13 Oct '07Published in: Organic Letters
The parent dendralene and 2-substituted dendralenes are made easily through cross-coupling reactions. Contrary to some earlier reports, dendralene is sufficiently stable to be handled using standard synthetic methods. These compounds allow the one-step stereoselective construction of polycyclic frameworks through reactions with dienophiles. Site selectivity and stereoselectivity in Diels-Alder reactions with dienophiles are generally not influenced by the nature of the dendralene's 2-substituent; these features can, however, be influenced with Lewis acids.