Catalytic asymmetric synthesis of palmerolide A via organoboron methodology.
A catalytic enantioselective synthesis of the antimelanoma marine natural product (-)-palmerolide A was accomplished using a longest sequence of 21 steps and without resorting to stoichiometric chiral auxiliaries or the chiral pool. The right half was constructed with a new variant of the Claisen-Ireland rearrangement exploiting an alkenylboronate as a masked hydroxyl. The left half featured the first application of a diol.SnCl(4)-catalyzed enantioselective crotylboration in the context of a complex target. This distinct strategy could pave the way to the design of simplified analogues of palmerolide.
Penner
Marlin
M
Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada.
Rauniyar
Vivek
V
Kaspar
Ludwig T
LT
Hall
Dennis G
DG
D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001896:Boron Compounds; D018942:Macrolides; C522534:palmerolide A