Cross-coupling for cross-conjugation: practical synthesis and Diels-Alder reactions of [3]dendralenes.

Research paper by Tanya A TA Bradford, Alan D AD Payne, Anthony C AC Willis, Michael N MN Paddon-Row, Michael S MS Sherburn

Indexed on: 13 Oct '07Published on: 13 Oct '07Published in: Organic Letters


The parent [3]dendralene and 2-substituted [3]dendralenes are made easily through cross-coupling reactions. Contrary to some earlier reports, [3]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 [3]dendralene's 2-substituent; these features can, however, be influenced with Lewis acids.