4-[(4'-Methylphenyl)sulfonyl]-1-(trophenylphosphoranylidene)-2-butanone as a New Four-Carbon Synthon for Substituted Divinyl Ketones
The title compound and the corresponding anion have been conveniently used as precursors of substituted divinylketones in both carbo- and heterocyclization reactions in one-pot, three-step sequences leading to a wide variety of substituted carbo- and heterocyclic ring systems, as well as to multifunctionalized linear carbon frameworks. The compounds generated through the use of this multi-coupling reagent represent useful synthons for the construction of natural compounds including (+/-)-epibatidine, (-)-anabasine and (+/-)-pyrenophorin.
Barco, Achille,Benetti, Simonetta,Risi, Carmela De,Marchetti, Paolo,Pollini, Gian Piero,Zanirato, Vinicio
p. 975 - 986
(2007/10/03)
Total Syntheses of Wyerone and Dihydrowyerone, Phytoalexins from the Broad Bean, Vicia faba L., using the Dianion derived from 3-(2-Furyl)acrylic Acid
Treatment of 3-(2-furyl)acrylic acid (8) with lithium di-isopropylamide at low temperatures gives lithium 3-(5-lithio-2-furyl)acrylate (9).This has been used to prepare the broad bean metabolites wyerone (1) and dihydrowyerone (2) by condensations with (Z
Knight, David W.,Nott, Andrew P.
p. 623 - 626
(2007/10/02)
The Reaction on 2-Methylfuran with Methyl Acrylate Unusual Formation of 1,2'-Bis(5-methyl-2-furyl)ethane and Methyl 3,3'-Bis(5-methyl-2-furyl)propionate
The reaction of 2-methylfuran with methyl acrylate in the presence of Pd(OAc)2 gave unusual products such as 1,1'-bis(5-methyl-2-furyl)ethane (22percent) and methyl 3,3'-bis(5-methyl-2-furyl)propionate (10percent) along with the usual aromatic substitution product.This is a marked contrast to the reaction of furan with olefins.
Maruyama, Osamu,Fujiwara, Yuzo,Taniguchi, Hiroshi
p. 2851 - 2852
(2007/10/02)
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