Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.
Neighbors, Jeffrey D.,Buller, Matthew J.,Boss, Kelly D.,Wiemer, David F.
experimental part
p. 1949 - 1952
(2009/09/06)
Total synthesis of (±)-Sigmoidin-A [3′,4′,5,7-tetrahydroxy-2-(γ,γ-dimethylallyl)flavanone] and of antiarone-F
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Zhao, Lianyun,Li, Yulin
p. 165 - 171
(2007/10/03)
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