56197-54-7Relevant articles and documents
Biosynthesis of the Hypotensive Metabolite Oudenone by Oudemansiella radicata. 1. Intact Incorporation of a Tetraketide Chain Elongation Intermediate
Tsantrizos, Youla S.,Zhou, Fei,Famili, Parsa,Yang, Xianshu
, p. 6922 - 6929 (1995)
The biosynthesis of the fungal metabolite oudenone (1) was investigated in cultures of Oudemansiella radicata.Feeding experiments using 13C- and 2H-labeled precursors, as well as NMR analyses of the labeled metabolite, suggested a polyketide origin.The incorporation of six acetate units into the carbon skeleton of 1 was observed when cultures were fed the N-acetylcysteamine thioester derivative of 13C-labeled acetate.Labeling of oudenone (1) from succinate or L-glutamic acid was not observed, whereas the pattern of 13C labeling from succinate was identical to that observed with acetate.The proposed advanced intermediate (5S)-5-hydroxyoctanoic acid (2) was synthesized as the deuterium labeled N-acetylcysteamine thioester derivative (S)-19 and successfully incorporated into 1.A biosynthetic scheme and cyclization mechanism, consistent with the experimental data, is proposed.
CYCLOPENTANE CARBOXYLATE COMPOUNDS, PROCESS AND INTERMEDIATES FOR PREPARING THE SAME AND USE THEREOF
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Page/Page column 21, (2010/11/08)
The present invention discloses cyclopentane carboxylate compounds. The I-hydrocarbyl-2-acyloxy-cyclopentane carboxylates according to the invention have a general formula (I): wherein groups R1, R2 and R3, which are ident
Electroorganic Chemistry. 124. Electroreductive Intramolecular Coupling of α-(ω-Bromoalkyl) β-Keto Esters
Shono, Tatsuya,Kise, Naoki,Uematsu, Nobuyuki,Morimoto, Shinji,Okazaki, Eiichi
, p. 5037 - 5041 (2007/10/02)
Intramolecular coupling occurs when cyclic α-(bromomethyl) β-keto esters are electrochemically reduced in the presence of trimethylsilyl chloride and one-carbon ring-enlarged products are obtained in reasonable yields.Electroreduction of α-(γ-bromopropyl) β-keto esters also affords the corresponding five-membered cyclized products and/or the corresponding ring-opened compounds.The ease of ring opening of the cyclized products is highly influenced by their stereoconfiguration.Electroreduction of α-(β-bromoethyl) β-keto ester gives the product formed by the reductive elimination of the bromoethyl group whereas α-(δ-bromobutyl) β-keto ester yields the product of the reductive elimination of bromine.This electroreductive intramolecular coupling is initiated by the reduction of the carbon-bromine bond and proceeds through a carbanion intermediate.