Synthetic studies on the bryostatins: synthetic routes to analogues containing the tricyclic macrolactone core.
[reaction: see text]. 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.
Keck
Gary E
GE
Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112-0850, USA. keck@chemistry.utah.edu
Truong
Anh P
AP
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D054713:Bryostatins; D002384:Catalysis; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry*; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*
D000970:Antineoplastic Agents; D054713:Bryostatins; D007783:Lactones; D018942:Macrolides; D011714:Pyrans; C046785:bryostatin 1