616866-48-9Relevant articles and documents
Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions
Goodenough, Katharine M.,Moran, Wesley J.,Raubo, Piotr,Harrity, Joseph P. A.
, p. 207 - 213 (2007/10/03)
(Chemical Equation Presented). In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.