An enantioselective synthesis of cryptocarya diacetate.
[reaction: see text]. The enantioselective synthesis of cryptocarya diacetate has been achieved in 10 steps from ethyl sorbate. The route relies upon an enantio- and regioselective Sharpless dihydroxylation and a palladium-catalyzed reduction to form a delta-hydroxy-1-enoate, which was subsequently converted into a benzylidene-protected 3,5-dihydroxy carboxylic ester. This ester was converted into cryptocarya diacetate in 14% overall yield via an allylation and methathesis ring closure reaction sequence.
Hunter
T J
TJ
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
O'Doherty
G A
GA
D000085:Acetates / Q000138:chemical synthesis*; D019770:Lauraceae / Q000737:chemistry*; D013237:Stereoisomerism
D000085:Acetates