Total synthesis of enantiopure (+)-gamma-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation.
[reaction: see text] A highly efficient short total synthesis of (+)-gamma-lycorane (>99% ee, 41% overall yield) was achieved by using the asymmetric allylic alkylation in the key step catalyzed by palladium complexes with novel chiral biphenol-based monodentate phosphoramidite ligands.
Chapsal
Bruno D
BD
Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA.
Ojima
Iwao
I
D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
D000498:Allyl Compounds; D047151:Amaryllidaceae Alkaloids; C412290:lycorane; D010165:Palladium