Amino acids. 8. A novel synthesis of .gamma.-carboxy-L-glutamic acid from L-5-oxoproline esters

Effenberger, Franz; Mueller, W. H.; Keller, Roland; Wild, W.; Ziegler, Thomas

doi:10.1021/jo00297a022

Cited by 21 publications

(5 citation statements)

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“…Diphenylmethylamine (21) underwent the 4CR with good dr, and its cleavage was effected in modest (62%) yield using TFA. Attempted cleavage by hydrogenolysis was ineffective (24). The introduction of p-methoxy groups to both phenyl rings in the form of dianisylmethylamine (DAM-NH 2 , 22) (25) resulted in higher yield and lower diastereoselectivity for the 4CR as well as high yield for the cleavage reaction (91%).…”

mentioning

confidence: 99%

Ammonia synthons for the multicomponent assembly of complex γ-lactams

Tan

Martin

Fettinger

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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The synthesis of γ-lactams that are unsubstituted at the 1-position (nitrogen) as well as their subsequent N -functionalization is reported. A recently discovered four-component reaction (4CR) is employed with either an ammonia precursor or a protected form of ammonia that can be deprotected in a subsequent synthetic step. These methods represent the first multicomponent assembly of complex lactam structures that are unsubstituted at nitrogen. In addition, two methods for the introduction of nitrogen substituents that are not possible through the original 4CR are reported. X-ray crystallographic analysis of representative structures reveals conformational changes in the core structure that will enable future deployment of this chemistry in the design and synthesis of diverse collections of lactams suitable for the discovery of new biological probes.

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mentioning

confidence: 99%

Ammonia synthons for the multicomponent assembly of complex γ-lactams

Tan

Martin

Fettinger

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

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“…22 The carboxylic acid derivative 7 was prepared by oxidation of the compound 6 with manganese oxide followed by silver nitrate in basic conditions. Hydrogenation of α-cyperone 1 using Pd-C in methanol 23 gave compound 4 where the double bond at the C7 position was reduced. All α-cyperone derivatives were characterized by NMR and MS.…”

Section: 8mentioning

confidence: 99%

Syntheses of 7-Substituted α-Cyperone Derivatives for Selective Sigma-1 Receptor over Cannabinoid-1 Receptor Binding Affinities

Park¹,

Shin²,

Kim

et al. 2013

Bulletin of the Korean Chemical Society

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“…This was also confirmed by HPLC on an analytical column (MeCN-H 2 O 60 : 40). The fresh solution had a t R of 15.88 min which changed after 3 h to t R 15…”

Section: N-(benzyloxycarbonyl)dehydroalanine Benzyl Estermentioning

confidence: 99%