A Diels–Alder approach for the synthesis of highly functionalized benzo-annulated indane-based α-amino acid derivatives via a sultine intermediate

Kotha, Sambasivarao; Ghosh, Arun K.

doi:10.1016/j.tetlet.2004.02.060

Cited by 35 publications

(10 citation statements)

References 35 publications

(6 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…By adopting this strategy, a new a,a-dialkylatedindane-based [60]fullerene containing a rigid AAA unit 112 was realized (Scheme 20). 33 A Diels-Alder approach has been developed to prepare dicarba analogues of cystine. Treatment of diene 113 with [60] fullerene in toluene at reux furnished the stable cycloadduct 114 in good yield (Scheme 21).…”

Section: Assocmentioning

confidence: 99%

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

2014

View full text Add to dashboard Cite

This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides. The applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted. This review reports on the latest progress in the synthesis of fullerenyl amino acids and related derivatives, and categorises the molecules into functional types for different uses: these include directly attached fullerenyl amino acids, fullerenyl N-and C-capping amino acids, and those amino acids in which the [60]fullerene group is attached to the amino acid side chain. These first and last mentioned derivatives have the potential to be incorporated into non-terminal positions of peptides. Disciplines Medicine and Health Sciences | Social and Behavioral SciencesThe applications of these substrates, by integration into different biological and materials chemistry programs, are also highlighted.

show abstract

Section: Assocmentioning

confidence: 99%

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

2014

View full text Add to dashboard Cite

show abstract

“…Under cobalt catalyst conditions, bulky alkynes such as BTMSA and diphenylacetylene also gave the required co‐trimerized products. The dihydroxy derivative 180a was found to be useful for production of the o ‐xylylene intermediate103b suitable for further annulation sequence 103c,103d…”

Section: Application Of [2+2+2] Cycloadditions In Organic Synthesismentioning

confidence: 99%

Transition Metal Catalyzed [2+2+2] Cycloaddition and Application in Organic Synthesis

2005

Self Cite

View full text Add to dashboard Cite

The [2+2+2] cycloaddition strategy is complementary to the well known Diels-Alder reaction for the generation of polycyclic compounds. This [2+2+2] approach is atom-economical and, with the availability of new catalysts to effect the [2+2+2] cycloaddition reaction, synthesis of a wide variety of highly functionalized polycycles is possible. This review deals with some recent advances relating to [2+2+2] cycloaddition reactions involving the syntheses both of polycycles

show abstract

“…In 2004, we also reported indane‐based AAA derivatives such as 353 and 354 bearing C 60 ‐moiety by adopting the DA strategy as a key step (Scheme ) . The polycycle 358 having a crown ether moiety was synthesized by adopting the DA reaction of sulfone derivative 356 (Scheme ) …”

Section: Rongalitementioning

confidence: 99%

Development of New Synthetic Strategies, Tactics and their Applications

Kotha

Meshram

2019

The Chemical Record

Self Cite

View full text Add to dashboard Cite

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.

show abstract

A Diels–Alder approach for the synthesis of highly functionalized benzo-annulated indane-based α-amino acid derivatives via a sultine intermediate

Cited by 35 publications

References 35 publications

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

[60]Fullerenyl amino acids and peptides: a review of their synthesis and applications

Transition Metal Catalyzed [2+2+2] Cycloaddition and Application in Organic Synthesis

Development of New Synthetic Strategies, Tactics and their Applications

Contact Info

Product

Resources

About