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Asymmetric Total Synthesis of Laurallene
Fumihiko Yoshimura1, Taku Okada2, Keiji Tanino1
1Department of Chemistry, Faculty of Science , Hokkaido University , Sapporo 060-0810 , Japan.
Abstract:
The asymmetric total synthesis of laurallene was achieved in 13 steps for the longest linear sequence with 3.3% overall yield from commercially available trans-2-pentenal. This synthesis features the highly efficient construction of a branched ether system with five oxygenated asymmetric stereocenters by the combination of a palladium-catalyzed alkoxy substitution reaction and a cobalt-catalyzed Mukaiyama oxidative cyclization.
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