Constrained Phenylalanine Derivatives by Enyne Metathesis and Diels−Alder Reaction

Kotha, Sambasivarao; Sreenivasachary, Nampally; Brahmachary, Enugurthi

doi:10.1002/1099-0690(200102)2001:4<787::aid-ejoc787>3.3.co;2-e

Cited by 22 publications

(28 citation statements)

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“…41) In other words, the acid 10 was converted to a diiodide (11) by reduction with LiAlH 4 , and subsequent substitution with iodide. Then, ethyl isocyanoacetate was bisalkylated with 11, 42) followed by acidic hydrolysis and protection of the N-terminus with Boc 2 O to afford amino acid Boc-[(R,R)-Ab 5,6ϭ c]-OEt in 59% yield. The N-terminal protecting group, and the C-terminal ester group could be quantitatively deprotected, respectively, and the N-terminal and C-terminal free amino acids were used for peptide synthesis.…”

Section: Design and Synthesis Of A Chiral Bicyclic A Aa A-disubstitumentioning

confidence: 99%

Design and Synthesis of Chiral .ALPHA.,.ALPHA.-Disubstituted Amino Acids and Conformational Study of Their Oligopeptides

Tanaka

2007

Chem. Pharm. Bull.

248

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Section: Design and Synthesis Of A Chiral Bicyclic A Aa A-disubstitumentioning

confidence: 99%

Design and Synthesis of Chiral .ALPHA.,.ALPHA.-Disubstituted Amino Acids and Conformational Study of Their Oligopeptides

Tanaka

2007

Chem. Pharm. Bull.

248

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“…Along similar lines, in 2001, we have also extended the same strategy toward the synthesis of indane‐based AAA derivatives containing‐crown ether using EICA and the corresponding dihalo derivatives (Scheme ) …”

Section: α‐Amino Acidsmentioning

confidence: 88%

Development of New Synthetic Strategies, Tactics and their Applications

Kotha

Meshram

2019

The Chemical Record

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This account covers our work related to the development of various synthetic methodologies since 1994. We summarized our strategies and their application to design various functional molecules. In this regard, we also report the utility of our methodologies in others research work. These methods we report here are simple and efficient for the synthesis of a wide variety of intricate molecules such as heterocycles, polycycles, unusual α‐amino acids, star‐shaped molecules, and modified peptides. For this purpose, we used various transition metal‐based reagents and catalysts. Various popular reactions such as metathesis, Suzuki coupling, [2+2+2] cyclotrimerization were used to assemble these targets. Moreover, rongalite has been used to expand the Diels‐Alder chemistry.

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“…Therefore, a conceptually new approach for the synthesis of indanebased glycine derivatives via enyne metathesis and the Diels-Alder reaction as key steps was planned. 41,42 To this end, the five-membered ring building block 119 containing an a-amino acid moiety was prepared by enyne metathesis of 118 (Scheme 23). Because it is difficult to control stepwise alkylation with ethyl isocyanoacetate, benzophenone Schiff base 116 was used as a starting material as it is known to undergo stepwise alkylation under PTC conditions.…”

Section: Application Of Enyne Metathesis To the Synthesis Of Constrained A-amino Acid And Naphthoxepin Derivativesmentioning

confidence: 99%

Synthesis of Diverse Polycyclic Compounds via Catalytic Metathesis

Kotha¹,

Lahiri²

2007

Synlett

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114

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A variety of olefin-metathesis protocols have been used to prepare spirocyclic compounds, cyclic sulfones, and constrained a-amino acid derivatives. Conceptually, a new approach to a novel cyclophane ring system has been realized via ring-closing metathesis (RCM). Also, tetracyclic compounds related to anthracycline antibiotics have been assembled using Claisen rearrangement and RCM as key steps. Further, a sequential use of the Diels-Alder reaction and ring-opening cross-metathesis delivered highly functionalized spiroindane derivatives, and trisubstituted benzene derivatives have been assembled using Grubbs' catalyst. Finally, the enyne and cross-enyne metathesis sequences have been used to prepare several constrained a-amino acid derivatives. 10 Synthesis of Trisubstituted Benzene Derivatives Using Grubbs' Catalyst 11 Metathesis of a Novel Enyne System 12 Macroheterocycles via Cross-Enyne and Ring-Closing Metathesis Cascade Reactions 13 Conclusions

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Constrained Phenylalanine Derivatives by Enyne Metathesis and Diels−Alder Reaction

Cited by 22 publications

References 0 publications

Design and Synthesis of Chiral .ALPHA.,.ALPHA.-Disubstituted Amino Acids and Conformational Study of Their Oligopeptides

Design and Synthesis of Chiral .ALPHA.,.ALPHA.-Disubstituted Amino Acids and Conformational Study of Their Oligopeptides

Development of New Synthetic Strategies, Tactics and their Applications

Synthesis of Diverse Polycyclic Compounds via Catalytic Metathesis

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