Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water† †Electronic supplementary information (ESI) available: Experimental procedures; NMR characterisation; LC-MS characterisation. See DOI: 10.1039/c6sc04423a Click here for additional data file.
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چکیده
Experimental For the synthesis of: Sodium 2'-(Dicyclohexylphosphanyl)-2,6-diisopropyl-(1,1-biphenyl)-4-sulfonate (sXPhos) 12 4 Standard Reaction Procedure of 5-bromoindole 15 under reflux: 5 Microwave Reaction Procedure of 5-bromoindole 15: 5 Standard Microwave Reaction Procedure for Tryptophans: 5 (S)-2-Amino-3-(5-(phenylethynyl)-1H-indol-3-yl)propanoic acid 19 6 (S)-2-Amino-3-5-((3-fluorophenyl)ethynyl)-1H-indol-3-yl)propanoic acid 36 7 (S)-2-Amino-3-5-((4-cyanophenyl)ethynyl)-1H-indol-3-yl)propanoic acid 39 7 (S)-2-Amino-3-(5-(thiophen-3-ylethynyl)-1H-indol-3-yl)propanoic acid 42 8 (S)-2-Amino-3-(5-(4-hydroxybut-1-yn-1-yl)-1H-indol-3-yl)propanoic acid 45 9 (S)-2-Amino-3-(5-(4-phenylbut-1-yn-1-yl)-1H-indol-3-yl)propanoic acid 48 9 (S)-2-Amino-3-(5-(octa-1,7-diyn-1-yl)-1H-indol-3-yl)propanoic acid 51 10 (S)-2-Amino-3-(3-cyclohexylprop-1-yn-1-yl)-1H-indol-3-yl)propanoic acid 54 10 N-Boc-7-bromo-S-tryptophan 66 11 7-Bromo-L-tryptophan methyl ester hydrochloride 67 12 N-Boc-Ala-Phe-OMe 68 12 H-Ala-Phe-OMe.TFA 69 13 N-Boc-Trp-(7-Br)-Ala-Phe-OMe 70 14 H-Trp-(7-Br)-Ala-Phe-OH 59 15 N-Boc-Trp-(7-Br)-Phe-OMe 71 16 N-Boc-Ala-Trp-(7-Br)-Phe-OMe 72 17 H-Ala-Trp-(7-Br)-Phe-OH 58 18 ((S)-2-((S)-2-Aminopropanamido)-3-(7-((3-fluorophenyl)ethynyl)-1H-indol-3-yl)propanoyl)-Lphenylalanine 60 19 ((S)-2-Amino-3-(7-((3-fluorophenyl)ethynyl)-1H-indol-3-yl)propanoyl) -L-alanyl-L-phenylalanine 61 20 Enantiopurity analysis 21
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Sonogashira diversification of unprotected halotryptophans, halotryptophan containing tripeptides; and generation of a new to nature bromo-natural product and its diversification in water.
The blending together of synthetic chemistry with natural product biosynthesis represents a potentially powerful approach to synthesis; to enable this, further synthetic tools and methodologies are needed. To this end, we have explored the first Sonogashira cross-coupling to halotryptophans in water. Broad reaction scope is demonstrated and we have explored the limits of the scope of the reacti...
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