Total Synthesis of Discodermolide: Optimization of the Effective Synthetic Route (pages 11092–11112)
Elsa de Lemos, François-Hugues Porée, Arnaud Bourin, Julien Barbion, Evangelos Agouridas, Marie-Isabelle Lannou, Alain Commerçon, Jean-François Betzer, Ange Pancrazi and Janick Ardisson
Article first published online: 30 OCT 2008 | DOI: 10.1002/chem.200801478
An efficient and modulable total synthesis of discodermolide (DDM), a unique marine anticancer polyketide, is described including related alternative synthetic approaches. Key steps included the application of a crotyltitanation reaction to yield homoallylic (Z)-O-ene-carbamate alcohols with excellent selectivity and the installation of the C13C14 (Z) double bond through a highly selective dyotropic rearrangement (see scheme).