Benz[f]tryptophan, a bathochromic analog of tryptophan, synthesis of its N-α-t-boc derivative

Yokum, T. S.; Tungaturthi, Parithosh K.; McLaughlin, Mark L.

doi:10.1016/s0040-4039(97)01139-8

Cited by 17 publications

(14 citation statements)

References 9 publications

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“…The N-allylindole can be deprotected with Pd. 132 This new synthesis has been used to prepare a novel benzo[ f ]indole amino acid as a fluorescent probe, 133 and Bailey has extended the reaction to include the intermediacy of aryne intermediates in the sequence, the result being that the alkyllithium used to generate the aryne is incorporated into the cyclized indoline at the C-4 position. indole nitrogen can be readily deprotected (Mg-MeOH) and further functionalized as desired (acylation, alkylation).…”

Section: Bailey-liebeskind Indole Synthesismentioning

confidence: 99%

Recent developments in indole ring synthesis—methodology and applications

Gribble

2000

J. Chem. Soc., Perkin Trans. 1

960

294

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Section: Bailey-liebeskind Indole Synthesismentioning

confidence: 99%

Recent developments in indole ring synthesis—methodology and applications

Gribble

2000

J. Chem. Soc., Perkin Trans. 1

960

294

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“…The condensation reaction gave poor, but acceptable yields of benz[ f ]indole as other routes gave good yields of 3-substituted derivatives. For instance, the palladium-catalyzed hydroarylation of 1-trimethylsilylpropyne with 3-bromo-2-aminonaphthalene provides a good yield of 3-methylbenz[ f ]indoles. ,, …”

Section: Resultsmentioning

confidence: 99%

“…For instance, the palladium-catalyzed hydroarylation of 1-trimethylsilylpropyne with 3-bromo-2-aminonaphthalene provides a good yield of 3-methylbenz[f]indoles. 17,20,21 Absorption and Fluorescence Spectra. Figure 1 shows the absorption and fluorescence emission spectra of benzindole and 3-methylbenzindole in 10% CH 3 OH.…”

Section: Resultsmentioning

confidence: 99%

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Fluorescence Properties of Benz[f]indole, a Wavelength and Quenching Selective Tryptophan Analog

Liu¹,

Barkley²,

Morales³

et al. 2000

J. Phys. Chem. B

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Tryptophan analogues with unique spectral and photophysical properties offer intrinsic fluorescent probes for studying peptide-protein and protein-protein interactions. Two benzannulated indole derivatives, benz-[f]indole and 3-methylbenz[f]indole, were synthesized and their fluorescence was characterized. The absorption and fluorescence emission spectra are red shifted about 75 nm to the red of the spectra of indole and 3-methylindole. INDO/S-CIS computations indicate two nearly degenerate lowest excited singlet states, analogous to the 1 L a and 1 L b transitions of indoles but with almost collinear transition moments. The limiting excitation anisotropy spectra increase and the emission anisotropy spectra decrease with increasing wavelength, probably due to vibronic coupling of the 1 L a state with higher energy B states. Solvent and temperature effects on the wavelength of maximum emission argue that emission occurs from 1 L a in polar environments. The fluorescence quantum yields and lifetimes are high and essentially independent of temperature and solvent isotope. Quantum yields are 0.80 for both compounds. Lifetimes are 19 ns for benz[f]indole and 25 ns for 3-methylbenz[f]indole. The fluorescence is not quenched by most protein functional groups in Stern-Volmer experiments, though it is quenched weakly by strong electron acceptors, such as histidine and cysteine. These results indicate that two nonradiative processes of indoles, solvent quenching and excited-state proton transfer, are not important decay pathways of benzannulated indoles. A third nonradiative process, excited-state electron transfer, occurs in benzannulated indoles under more limited conditions than in indoles.

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“…Yield of isolated product and diastereomeric ratio (dr) in parenthesesIn addition to the tryptophan derivatives assembled in table 5, two other important tryptophan analogues were pursued via a similar cross-coupling/N-heteroannulation strategy: D-homotryptophan and D-isotryptophan. Multistep syntheses of the racemic form of these two tryptophan analogues have been reported previously;130 however, Cook et. al 99.…”

mentioning

confidence: 98%

The synthesis of tryptophan derivatives, 2- and/or 3-substituted indoles, progress toward dilemmaones A-C, and synthetic studies towards fistulosin via palladium-catalyzed reductive N-heteroannulation

Dacko¹

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Palladium-catalyzed carbon monoxide-mediated reductive N-heteroannulation of o-nitrostyrenes has emerged as a very powerful method for constructing the corresponding indole core. The Söderberg variety of this methodology has been utilized to synthesize several asymmetric tryptophan derivatives along with a collection of 2and/or 3-substituted indoles. The same protocol has also been employed to make synthetic progress toward the construction of the marine indole alkaloids Dilemmaones A-C. Finally, this versatile cyclization was implemented in studies designed to determine the true structure of the compound isolated by Tomita et. al. and given the name "fistulosin". iii Acknowledgments This work is dedicated to my grandparents, Andrew and Helen Dacko, and also to my good friend Jon Murt, all of whom passed away during my time as a graduate student at West Virginia University. I miss them all very dearly and wish they could have been here to witness my accomplishments. I would like to thank my advisor, Dr. Björn Söderberg, for his constant guidance, patience, and friendship during my graduate studies. I owe my development as a chemist to his counseling and support. I would also like to thank the faculty members in the C.

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Benz[f]tryptophan, a bathochromic analog of tryptophan, synthesis of its N-α-t-boc derivative

Cited by 17 publications

References 9 publications

Recent developments in indole ring synthesis—methodology and applications

Recent developments in indole ring synthesis—methodology and applications

Fluorescence Properties of Benz[f]indole, a Wavelength and Quenching Selective Tryptophan Analog

The synthesis of tryptophan derivatives, 2- and/or 3-substituted indoles, progress toward dilemmaones A-C, and synthetic studies towards fistulosin via palladium-catalyzed reductive N-heteroannulation

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