Polyalkyl furans are widespread in nature,o ften performing important biological roles.D espite ap lethora of methods for the synthesis of tetrasubstituted furans,t he construction of tetraalkylf urans remains non-trivial. The prevalence of alkylgroups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkylf urans, calls for ageneral synthetic protocol for polyalkylfurans.This paper describes aM ichael-Heck approach, using sequential phosphine-palladium catalysis,f or the preparation of various polyalkylf urans from readily available precursors.T he versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes,n amely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran;the marine natural products plakorsins A, B, and Dand plakorsin Dmethyl ester;and the furan fatty acids 3D5 and hydromumiamicin.
Polyalkyl furans are widespread in nature,o ften performing important biological roles.D espite ap lethora of methods for the synthesis of tetrasubstituted furans,t he construction of tetraalkylf urans remains non-trivial. The prevalence of alkylgroups in bioactive furan natural products, combined with the desirable bioactivities of tetraalkylf urans, calls for ageneral synthetic protocol for polyalkylfurans.This paper describes aM ichael-Heck approach, using sequential phosphine-palladium catalysis,f or the preparation of various polyalkylf urans from readily available precursors.T he versatility of this method is illustrated by the total syntheses of nine distinct polyalkylated furan natural products belonging to different classes,n amely the furanoterpenes rosefuran, sesquirosefuran, and mikanifuran;the marine natural products plakorsins A, B, and Dand plakorsin Dmethyl ester;and the furan fatty acids 3D5 and hydromumiamicin.
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