Synthesen von Peptidalkaloiden, 11. Über Aminosäuren und Peptide, 51. — Dehydroaminosäuren, 19. Totalsynthese von Hexaacetylcelenamid A

Schmidt, Ulrich; Wild, Jochen

doi:10.1002/jlac.198519850915

Cited by 23 publications

(8 citation statements)

References 17 publications

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“…27 As an alternative, concentrated hydrochloric acid or dry hydrogen chloride was added to the reaction mixture just after filtering off the catalyst. 27,45 In situ derivatization of amino ketones was accomplished by adding acetic anhydride 61 or di-tert-butyl dicarbonate (Boc anhydride) 48 to the solution of the substrate prior to the hydrogenation. Acetylation 61 or aroylation by an active ester 49 immediately after the reduction has also been reported.…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

“…Acetylation 61 or aroylation by an active ester 49 immediately after the reduction has also been reported. Hydrogenation in the presence of Pd-C was performed most often in alcohols (methanol or ethanol), 16,27,54,63 acetic acid 27,61 or 1,4-dioxane 48,49 have also been applied in some cases. The reported yields of the desired a-amino ketones were usually good (65-94%).…”

Section: Miscellaneous Methodsmentioning

confidence: 99%

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Syntheses and transformations of α-azido ketones and related derivatives

2011

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Organic azides are known and utilized in the synthetic organic chemistry as amine precursors, potential sources of nitrenes, dipoles useful in 1,3-dipolar cycloadditions and starting materials of phosphoranes for a long time, and their literature has been overviewed by several authors. On the other hand, there are some special subclasses within the azides which possess peculiar and interesting properties differing from those of the majority and offering extra synthetic possibilities. In this critical review we wish to give an exhaustive overview on the synthesis and synthetic potential of α-azido ketones and related systems, an underestimated group of compounds. The enhanced acidity of the α-hydrogen offers various new synthetic applications including the creation of a new C-C bond, while the joint presence of the carbonyl and vinyl functions of α-azido-α,β-unsaturated ketones results in a special reactivity, too. Chemo- and stereoselectivity issues also represent important points which are discussed in detail. Finally, the usefulness of the titled derivatives in the synthesis of various heterocycles is reviewed (273 references).

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Section: Miscellaneous Methodsmentioning

confidence: 99%

Section: Miscellaneous Methodsmentioning

confidence: 99%

Syntheses and transformations of α-azido ketones and related derivatives

2011

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“…7). When Cbz-protected phosphonate 20 (Schmidt et al 1982, 1984; Schmidt and Wild 1985; Hamzavi et al 2003) was employed in the Wittig-Horner reaction with aldehyde 10 , Cbz-protected δ-azido-didehydro α-amino acid ester ( Z )- 21 was obtained in 81 % yield (calculated as traces of aldehyde 10 could not completely be removed). Stereoisomer ( E )- 21 could also be isolated in 3 % yield, and again, application of the established 1 H NMR criteria for the distinction of ( Z )- and ( E )-didehydro amino acids (Mazurkiewicz et al 2005) confirmed the stereochemical assignment.…”

Section: Resultsmentioning

confidence: 99%

A biomimetic domino reaction for the concise synthesis of capreomycidine and epicapreomycidine

2012

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The non-proteinogenic amino acids capreomycidine and epicapreomycidine are constituents of antibiotically active natural products, but the synthesis of these unusual cyclic guanidine derivatives is challenging. The biosynthesis of capreomycidine has therefore been employed as a guideline to develop a concise biomimetic synthesis of both epimeric amino acids. The resulting domino-guanidinylation-aza-Michael-addition reaction provides the most convenient access to these amino acids in racemic form. Attempts to dissect the domino reaction into two separate transformations for a stereocontrolled version of this synthetic approach have also been made. The synthesized didehydro-arginine derivatives with urethane-protected guanidine moieties did not undergo the aza-Michael-addition anymore. These results may have wider implications for the 1,4-addition of guanidines to α,β-unsaturated carbonyl compounds, particularly to didehydro amino acids.Electronic supplementary materialThe online version of this article (doi:10.1007/s00726-012-1309-8) contains supplementary material, which is available to authorized users.

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“…They have been employed in the synthesis of peptide natural products, e.g. azinomycins A and B, 14 (AE)-tunichrome An-1, 15 tunichromes Mm-1 and Mm-2, 16 hexaacetylcelenamide A, 17,18 clionamide, 19 etc. Also, some compounds of this class are effective glutathione transferase inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis

et al. 2015

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Synthesen von Peptidalkaloiden, 11. Über Aminosäuren und Peptide, 51. — Dehydroaminosäuren, 19. Totalsynthese von Hexaacetylcelenamid A

Abstract: Es wird die Totalsynthese des linearen Peptidalkaloids Hexaacetylcelenamid A (7) beschrieben. Schlüsselreaktionen sind zwei Kondensationen mit α‐(Dialkylphoshoryl)aminosäurederivaten 10 zum Aufbau der Dehydroaminosäure‐ und Dehydropeptidderivate 14 bzw. 17.

Cited by 23 publications

References 17 publications

Syntheses and transformations of α-azido ketones and related derivatives

Syntheses and transformations of α-azido ketones and related derivatives

A biomimetic domino reaction for the concise synthesis of capreomycidine and epicapreomycidine

Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis

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