Stereo- and regioselective synthesis of squalene tetraepoxide.
Squalene tetraepoxide, a putative biosynthetic precursor to a variety of oxacyclic triterpenoid natural products, has been efficiently synthesized by anionic coupling of two farnesol-derived diepoxides, which have arisen from electronic control of the regioselectivity in organocatalytic enantioselective epoxidations.
Tong
Rongbiao
R
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Boone
Matthew A
MA
McDonald
Frank E
FE
D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared; D013185:Squalene / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
C546108:squalene tetraepoxide; D013185:Squalene