Asymmetric catalysis route to anti,anti stereotriads, illustrated by applications.
A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.
Parker
Kathlyn A
KA
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794, USA. kparker@notes.cc.sunysb.edu
Xie
Qiuzhe
Q
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D004809:Ephedrine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides; D015394:Molecular Structure; D012694:Serine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D019086:Bridged Bicyclo Compounds, Heterocyclic; D047630:Depsipeptides; D007783:Lactones; D018942:Macrolides; C470816:callipeltin D; C449042:scytophycin C; C104057:aplyronine A; D012694:Serine; C041707:N-methylephedrine; D004809:Ephedrine