Concise formal synthesis of the bryostatin southern hemisphere (C17-C27).
An efficient synthesis of Hale and co-workers' C17-C27 bryostatin southern hemisphere intermediate has been accomplished in six steps and 33% overall yield from (R)-2-(benzyloxy)propanal. The synthesis features a one-pot DIBALH/HWE ester homologation as well as a novel acetonide rearrangement/glycal formation cascade.
Voight
Eric A
EA
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706-1396, USA.
Roethle
Paul A
PA
Burke
Steven D
SD
D054713:Bryostatins; D007783:Lactones / Q000138:chemical synthesis*; D018942:Macrolides; D008968:Molecular Conformation
D054713:Bryostatins; D007783:Lactones; D018942:Macrolides; C046785:bryostatin 1