De novo asymmetric synthesis of 8a-epi-swainsonine.
An enantioselective and diastereocontrolled approach to 8a-epi-d-swainsonine has been developed from achiral furfural. The key step to this synthesis was a one-pot procedure for the hydrogenolytic removal of two protecting groups and two intramolecular reductive amination reactions. The absolute stereochemistry was introduced by asymmetric Noyori reduction of furfuryl ketone. This route relies on diastereoselective palladium-catalyzed glycosylation to install the anomeric bond, and Luche reduction, diastereoselective dihydroxylation to set up the manno-stereochemistry of the indolizidine precursor.
Abrams
Jason N
JN
Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
Babu
Ravula Satheesh
RS
Guo
Haibing
H
Le
Dianna
D
Le
Jennifer
J
Osbourn
Joshua M
JM
O'Doherty
George A
GA
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013055:Spectrophotometry, Infrared; D017026:Swainsonine / Q000138:chemical synthesis* / Q000737:chemistry
D017026:Swainsonine