A facile conversion of arginine into β-homoarginine dipeptides

Bastiaans, H. M. M.; Alewijnse, Astrid E.; Baan, J. L. Van Der; Ottenheijm, H. C. J.

doi:10.1016/s0040-4039(00)78368-7

Cited by 10 publications

(3 citation statements)

References 4 publications

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“…Formylketene (335), generated by decomposition of diazomalondialdyde (334) in refluxing n-butyl vinyl ether, produced dihydro-γ-pyrone 336, which furnished γ-pyrone on treatment with acid. [266] (Acyl)(phenyl)ketenes from thermolyses of PhCOϪCN 2 ϪCOR were reacted with alkynyl ethers to give γ-pyrones and azulenones competitively, albeit in poor yield.…”

Section: Scheme 41 [2ϩ2] Cycloaddition Reactions Of Ketenes With Iminesmentioning

confidence: 99%

“…A convergent synthesis of the cyclodepsipeptide (ϩ)-jasplakinolide was based on homologation of Boc-tyrosine-OTBDMS. [334] The conversion of orthogonally protected arginine 438 into the homologue 439 [335] was used to prepare TAN 1057 (440), an antibiotic with strong activity against methicillin-resistant strains of Staphylococcus aureus (Scheme 53). [336] An approach to the peptide antibiotic (ϩ)-negamycin (443) has been reported which starts from 441 and proceeds by way of 442.…”

Section: Homologation Of α-Amino Acidsmentioning

confidence: 99%

“…Incorporation of β-amino acids into peptides N α -Boc-N γ -Z,Z-Arg-CHN 2 in the presence of α-amino esters (55Ϫ76%). [335] Repeated application of the Ag ϩ -induced Wolff rearrangement afforded peptides containing a sequence of up to six β-amino acids. [315] Highly efficient solid phase syntheses based on Fmoc-95 have been developed, 463 Ǟ 464.…”

Section: Homologation Of α-Amino Acidsmentioning

confidence: 99%

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100 Years of the Wolff Rearrangement

2002

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The conversion of α‐diazo ketones into ketenes, and products derived therefrom, was discovered by Wolff in 1902. Major applications of the Wolff rearrangement, such as the Arndt−Eistert reaction (homologation of carboxylic acids) and the ring contraction of cyclic ketones, have been with us for some while. Nevertheless, substantial progress has been made recently. The reaction mechanism has been explored by means of matrix isolation, time‐resolved spectroscopy, and computation. Full retention of configuration of the migrating group has been established by using enantioselective chromatography. The Arndt−Eistert reaction has witnessed a renaissance in the field of natural products, in particular β‐amino acids and β‐peptides. Ring‐contracting Wolff rearrangements and ketene cycloadditions have been applied in syntheses of increasingly complex, biologically active target molecules. These accomplishments, as well as unsolved problems, are addressed in the present review. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)

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Section: Scheme 41 [2ϩ2] Cycloaddition Reactions Of Ketenes With Iminesmentioning

confidence: 99%

Section: Homologation Of α-Amino Acidsmentioning

confidence: 99%

Section: Homologation Of α-Amino Acidsmentioning

confidence: 99%

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100 Years of the Wolff Rearrangement

2002

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Total Synthesis of TAN-1057 A/B, a New Dipeptide Antibiotic fromFlexibacter sp. PK-74

et al. 1998

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TAN‐1057 (1a, b) − a new natural dipeptide antibiotic active against methicillin resistant strains of Staphylococcus aureus − was synthesized starting from Nα, Nδ, Nω‐tri‐Z‐L‐arginine 20b via the corresponding diazoketone 21b. This upon photolysis rearranged to the ketene which was trapped by (±)‐2,4,5,6‐tetrahydro‐5‐methylamino‐2‐ureidopyrimidin‐4‐one (3) to yield the fully protected dipeptide 23 (30%). The latter was deprotected by hydrogenolysis to give the final compound as a mixture of two epimers − TAN‐1057A, B − isolated previously from a strain of Flexibacter sp. PK‐74. The intermediate 3 was prepared from 3‐amino‐2‐(N‐Z‐N‐methylamino)propionic acid methyl ester hydrochloride (16) and 2‐methyl‐2‐thiopseudobiuret hydroiodide (18) in one step in 35% yield.

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Diazo‐Mediated Homologation Reactions

Candeias

Albuquerque

2023

Homologation Reactions

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A facile conversion of arginine into β-homoarginine dipeptides

Cited by 10 publications

References 4 publications

100 Years of the Wolff Rearrangement

100 Years of the Wolff Rearrangement

Total Synthesis of TAN-1057 A/B, a New Dipeptide Antibiotic fromFlexibacter sp. PK-74

Diazo‐Mediated Homologation Reactions

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