Synthetic Studies on the Bryostatins:
Synthetic Routes to Analogues
Containing the Tricyclic Macrolactone
Core
Gary E. Keck* andAnh P. Truong
Department of Chemistry, University of Utah, 315 South 1400 East RM 2020,
Salt Lake City, Utah 84112-0850
keck@chemistry.utah.edu
Received March 9, 2005
Abstract:
Synthesis of the first of a projected series of bryostatin analogues has been accomplished in 26 steps and 2.2% overall yield. In this letter,
we detail two approaches to the structural core of these tricyclic macrolactone bryostatin analogues. The key features of the route include
BITIP-catalyzed asymmetric allylation reactions and Mukaiyama aldol reactions, a chelation-controlled allylation, pyran annulation reactions,
and macrolactonization.
