Use of Masked Quinones in Organic Synthesis: Efforts Directed Towards the Synthesis of Tropolonoid Natural Products

The application of quinone-derived substrates as building blocks for the synthesis of tropolonoid natural products is described. A preparation of the terpene β-dolabrin involving electrocyclic ring-opening of a bicyclo[4.l.0]heptenone enolate is outlined. A number of approaches to the recently characterized alkaloid imerubrine involving a highly efficient annelation procedure to form the benzazulenoid carbocyclic skeleton are also discussed. [Chemical structure; see abstract in scanned thesis for details.]