Total syntheses of (-)-pyrimidoblamic acid and P-3A are disclosed. Central to the convergent approach is a powerful inverse electron demand Diels-Alder reaction between substituted electron-deficient 1,2,3-triazines and a highly functionalized and chiral primary amidine, which forms the pyrimidine cores and introduces all necessary stereochemistry in a single step. Intrinsic in the convergent a...

Detailed kinetic analyses of inverse electron-demand Diels–Alder cycloaddition and nitrilimine-alkene/alkyne 1,3-diploar cycloaddition reactions were conducted and the reactions were applied for rapid protein bioconjugation. When reacted with a tetrazine or a diaryl nitrilimine, strained alkene/alkyne entities including norbornene, trans-cyclooctene, and cyclooctyne displayed rapid kinetics. To...

Many isoprenylated flavonoids have been isolated from Japanese mulberry tree (Moraceae). Among them, kuwanons G (1) and H (2) were the first isolated active substances exhibiting a hypotensive effect. These compounds are considered to be formed through an enzymatic Diels-Alder type reaction between an isoprenyl portion of an isoprenylphenol as the diene and an alpha, beta-double bond of chalcon...

Abstract The synthesis of substituted isoxazole–oxazole hybrids by the noncatalytic reaction methyl 2-diazo-2-(alkyl/aryl/hetarylisoxazol-5-yl)acetates with alkyl and aryl cyanides has been reported. According to DFT calculations, proceeds through intermediate formation a nitrile ylide its subsequent cyclization at carbonyl oxygen. acrylonitrile 2-diazo-2-(isoxazol-5-yl)acetate quite differentl...

Pyritides belong to the ribosomally synthesized and post-translationally modified peptide class of natural products that were recently genome-predicted are structurally defined by unique pyridine-containing macrocycles. Inspired their biosynthesis, proceeding through modification cycloaddition form heterocyclic core, we report chemical synthesis pyritide A2 involving pyridine ring from an amino...

Many isoprenylated flavonoids have been isolated from mulberry trees and related plants (Moraceae). Among them, kuwanons G (13) and H (14) were the first isolated active substances exhibiting a hypotensive effect from the Japanese Morus root bark. These compounds are considered to be formed through an enzymatic Diels-Alder reaction of a chalcone (15) and dehydro-kuwanon C (16) or its equivalent...

In this update on the Diels-Alder reaction we would like to present an overview on how this very important reaction has progressed in the last decade, since the last spate of monographs and reviews appeared in the literature, and which deal with the reaction in the overall sense. Initially we present the Diels-Alder reaction in a generalised form, much as discovered over seventy years ago, so t...

The furan heterocycle is a dienic reagent particularly suitable for the Diels-Alder reaction and maleimides represent a typical family of complementary reagents because of their strong dienophilic character. This paper reviews critically the studies devoted to the exploitation of the Diels Alder reaction between those moieties to synthesise macromolecular materials possessing different structur...

ABSTRACT The Diels-Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene yields a mixture of carbodiene Diels-Alder adducts. B3LYP/6-31G(d) simulations indicate that the conversion of addends into methyl (1R*,2S*,3S*,4R*)-2-nitro-3-(4-nitrophenyl)-bicyclo[2.2.1]hept-5-ene-2-carboxylate occurs via two-stage heterodiene Diels-Alder reaction and (in a second ...