Since the initial isolation and structure characterization of
rocaglamide by King and coworkers in 1982,9 the synthetic
challenges associated with this class of natural products,
including the construction of the densely functionalized cyclopenta[b]benzofuran
core and its five contiguous stereogenic
centers, have drawn the attention of the synthetic community.
While numerous elegant approaches towards the core of rocaglamide
and structurally related compounds have been reported,
the strategies developed by Taylor, Dobler, and Porco
represent the most convenient and thus the most widely utilized
routes both for the synthesis of rocaglamide and the development
of derivatives.8 In 1991, Taylor and coworkers reported the
synthesis of racemic rocaglamide in eight steps from the
benzofuran intermediate 33.