Synthetic studies on the bryostatins: preparation of a truncated BC-ring intermediate by pyran annulation.
[reaction: see text]. A synthesis of a potential BC-ring subunit (C9-C27) for bryostatin 1, a remarkably potent anticancer agent, has been developed in 16 steps and 18% overall yield. The key features of this route include a BITIP-catalyzed asymmetric allylation reaction, chelation-controlled allylations, a hydroformylation reaction, and a pyran annulation reaction.
Keck
Gary E
GE
Department of Chemistry, University of Utah, 315 South 1400 East RM 2020, Salt Lake City, Utah 84112-0850, USA.
Truong
Anh P
AP
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry*; D054713:Bryostatins; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000737:chemistry*
D000970:Antineoplastic Agents; D054713:Bryostatins; D018942:Macrolides; D011714:Pyrans; C046785:bryostatin 1