Toward the total syntheses of pepluanin A and euphosalicin: Concise route to a highly oxygenated cyclopentane as a common intermediate

Article abstract of DOI:10.1055/s-2004-834822

A substrate controlled asymmetric synthesis is described of a highly functionalized cyclopentanyl vinyl triflate which serves as an advanced intermediate in the total synthesis of the novel multidrug resistance reversing jatrophanes pepluanin A and euphosalicin. Key steps are a Claisen-Eschenmoser rearrangement followed by hydroxy-lactonization, intramolecular trans-lactonization, Davis hydroxylation and regioselective enoltriflate formation.