Improved synthesis of (+/-)-4,12-dihydroxy[2.2]paracyclophane and its enantiomeric resolution by enzymatic methods: planar chiral (R)- and (S)-phanol.
(+/-)-4,12-Dihydroxy[2.2]paracyclophane [(+/-)-PHANOL] is readily prepared from [2.2]paracyclophane by an improved synthetic protocol. Enzymatic kinetic resolution of its bis-acetate proceeds with good enantioselection. Separation, hydrolysis, and recrystallization provides both enantiomers of PHANOL in high enantiopurity.
Braddock
D Christopher
DC
Department of Chemistry, Imperial College of Science, Technology and Medicine, South Kensington, London, SW7 2AY UK. c.braddock@ic.ac.uk
MacGilp
Iain D
ID
Perry
Benjamin G
BG