99615-81-3Relevant academic research and scientific papers
Synthesis of N-(2-methylpropyl)-2E-undecene-8,10-diynamide, a novel constituent of Echinacea angustifolia
Kraus, George A.,Bae, Jaehoon
, p. 5505 - 5506 (2003)
The first synthesis of a diacetylenic amide from Echinacea is reported. The key steps included the reaction of an aldehyde with the monoanion of a diacetylene and the reductive removal of a propargylic alcohol.
Diacetylenic isobutylamides of Echinacea: Synthesis and natural distribution
Wu, Lankun,Bae, Jaehoon,Kraus, George,Wurtele, Eve Syrkin
, p. 2477 - 2484 (2004)
The syntheses of three diacetylenic isobutylamides of Echinacea and their distribution in nine Echinacea species are described. The syntheses of three diacetylenic isobutylamides of Echinacea angustifolia have been achieved by direct synthetic routes by way of a common intermediate. The key step is the alkylation of the anion of the silylated diacetylene. We report the presence of all three diacetylenic isobutylamides in six of the nine Echinacea species: E. angustifolia, E. sanguinea, E. simulata, E. tennesseensis, E. atrorubens and E. laevigata. The accumulation of these amides is sensitive to organ type and age.
Polyunsaturated alkyl amides from echinacea: Synthesis of diynes, enynes, and dienes
Matovic, Nicholas J.,Hayes, Patricia Y.,Penman, Kerry,Lehmann, Reginald P.,De Voss, James J.
, p. 4467 - 4481 (2011/07/30)
The synthesis of 20 alkyl amides, including 15 naturally occurring polyunsaturated alkyl amides previously identified from Echinacea spp. (1-13 and 62) or from Achilla sp. (55) and five previously unknown geometric isomers (23, 28, 67, 73, and 80), is described. Importantly, these amides include all of the major alkyl amides present in commercially used Echinacea extracts. The syntheses demonstrate methodology used for constructing alkyl amides containing conjugated diyne and isomerically pure enyne and diene moieties and may be adapted easily for the preparation of other alkyl amides present in Echinacea spp. Terminal-conjugated diynes were prepared by a Cadiot-Chodkiewitz coupling/deprotection sequence utilizing a protected bromoacetylene, and methyl-substituted diynes were made via a base-catalyzed rearrangement of terminal-skipped diynes. Conjugated dienes were prepared conveniently and with high stereoselectivity by the reduction of enynes or diynes with Rieke zinc. With the exception of 1-2 and 11-12, the alkyl amides are synthesized here for the first time, and their NMR data are consistent with that of the reported isolated natural compounds.
Synthesis of ynamides
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Page/Page column 4, (2008/06/13)
A method of synthesizing diacetylenic amides is described. The key steps of the invention include the reaction of an aldehyde with the monoanion of a diacetylene and the reductive removal of a propargylic alcohol. The invention offers the first known method of synthesizing diacetylenic amides that are naturally isolated from Echinacea through a direct and flexible route.
