A copper-carbodiimide approach to the phomopsin tripeptide side chain

Shangguan, Ning; Joullié, Madeleine M.

doi:10.1016/j.tetlet.2009.09.072

Cited by 33 publications

(40 citation statements)

References 23 publications

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“…xxi Beginning with commercially available pyrrolidine 33 , Mitsunobu inversion provided the cis -iodo proline derivative, 34 , in high yield (Scheme 6). xxii Nucleophilic displacement with selenobenzoic acid xxiii generated 35 in 84% yield. This intermediate displayed the key diagnostic 13 C resonance of ~200 ppm for a selenocarboxylate.…”

Section: Resultsmentioning

confidence: 99%

Advances in Proline Ligation

et al. 2012

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Section: Resultsmentioning

confidence: 99%

Advances in Proline Ligation

et al. 2012

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“…[31] Organocatalytic asymmetric aziridination of a-substituted a,b-unsaturated aldehydes: Encouraged by the above success, we became intrigued as to whether functionalized aziridines containing an a-tertiary amine stereocenter could be synthesized by a chiral amine-catalyzed reaction between asubstituted a,b-unsaturated aldehydes 1 [32][33] and a suitable nitrogen source 2. To our delight, when using 2 b as the reagent, the aziridination of 1 u proceeded smoothly in the presence of chiral pyrrolidine catalysts (10, 12, and 14) together with a base additive affording the corresponding product 3 cc in high conversion (Table 5).…”

Section: Resultsmentioning

confidence: 99%

Catalytic Asymmetric Aziridination of α,β‐Unsaturated Aldehydes

Deiana

Dziedzic

Zhao

et al. 2011

Chemistry A European J

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The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziridines with up to >19:1 d.r. and 99% ee. The aminocatalytic aziridination of α-monosubstituted enals gives access to terminal α-substituted-α-formyl aziridines in high yields and up to 99% ee. In the case of the organocatalytic aziridination of disubstituted α,β-unsaturated aldehydes, the transformations were highly diastereo- and enantioselective and give nearly enantiomerically pure β-formyl-functionalized aziridine products (99% ee). A highly enantioselective one-pot cascade sequence based on the combination of asymmetric amine and N-heterocyclic carbene catalysis (AHCC) is also disclosed. This one-pot three-component co-catalytic transformation between α,β-unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N-tert-butoxycarbonyl and N-carbobenzyloxy-protected β-amino acid esters with ee values ranging from 92-99%. The mechanisms and stereochemistry of all these catalytic transformations are also discussed.

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“…[11] Theb iosynthetic pathway of phomopsin Ai ncluding the formation of the didehydroaspartate moiety,h as not yet been elucidated. [11] Theb iosynthetic pathway of phomopsin Ai ncluding the formation of the didehydroaspartate moiety,h as not yet been elucidated.…”

Section: Methodsmentioning

confidence: 99%

Didehydroaspartate Modification in Methyl‐Coenzyme M Reductase Catalyzing Methane Formation

et al. 2016

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All methanogenic and methanotrophic archaea known to date contain methyl-coenzyme M reductase (MCR) that catalyzes the reversible reduction of methyl-coenzyme M to methane. This enzyme contains the nickel porphinoid F430 as a prosthetic group and, highly conserved, a thioglycine and four methylated amino acid residues near the active site. We describe herein the presence of a novel post-translationally modified amino acid, didehydroaspartate, adjacent to the thioglycine as revealed by mass spectrometry and high-resolution X-ray crystallography. Upon chemical reduction, the didehydroaspartate residue was converted into aspartate. Didehydroaspartate was found in MCR I and II from Methanothermobacter marburgensis and in MCR of phylogenetically distantly related Methanosarcina barkeri but not in MCR I and II of Methanothermobacter wolfeii, which indicates that didehydroaspartate is dispensable but might have a role in fine-tuning the active site to increase the catalytic efficiency.

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A copper-carbodiimide approach to the phomopsin tripeptide side chain

Cited by 33 publications

References 23 publications

Advances in Proline Ligation

Advances in Proline Ligation

Catalytic Asymmetric Aziridination of α,β‐Unsaturated Aldehydes

Didehydroaspartate Modification in Methyl‐Coenzyme M Reductase Catalyzing Methane Formation

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