Synthesis of the c14-c25 subunit of bafilomycin A1.
The enantioselective synthesis of the C14-C25 subunit of bafilomycin A1 was realized in a convergent route. The sequence involves two dynamic kinetic resolution steps of 2-alkyl 1,3-diketones that use optically active ruthenium complexes, an anti-selective reduction of a beta-hydroxyketone to control the C23 stereogenic center, and an aldol-type reaction under Evans' conditions, which sets the C17 and C18 stereogenic centers.
Eustache
Florence
F
Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris 05, France.
Dalko
Peter I
PI
Cossy
Janine
J
D007659:Ketones / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D007659:Ketones; D018942:Macrolides; D009942:Organometallic Compounds; D012428:Ruthenium; C040929:bafilomycin A1