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Tautomer formation. Data not shown
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Tautomer formation. Data not shown.
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See supporting information for details.
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In our hands, both 3-O-TMS- and TES-protected 3-hydroxypyridines were unstable to standard aqueous workup conditions as well as standard SiO 2-based purification TLC and flash column chromatography
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2-based purification (TLC and flash column chromatography).
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35
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34249814488
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All regioisomers have been unequivocally assigned by means of 2-D NMR data (DQF-COSY, HSQC, HMBC).
-
All regioisomers have been unequivocally assigned by means of 2-D NMR data (DQF-COSY, HSQC, HMBC).
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When compared with other α-amino acids, pseudo-prolines (ketal-protected serine, threonine and cysteine derivatives) have, such as proline itself, a much lower tendency to racemize at the α-carbon; for example see Wöhr, T.; Wahl, T.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X. C.; Mutter, M. J. Am. Chem. Soc. 1996, 118, 9218.
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When compared with other α-amino acids, pseudo-prolines (ketal-protected serine, threonine and cysteine derivatives) have, such as proline itself, a much lower tendency to racemize at the α-carbon; for example see Wöhr, T.; Wahl, T.; Nefzi, A.; Rohwedder, B.; Sato, T.; Sun, X. C.; Mutter, M. J. Am. Chem. Soc. 1996, 118, 9218.
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A different approach to the nosiheptide core structure has been detailed, (a) Umemura, K.; Noda, H.; Yoshimura, J.; Konn, A.; Yonezawa, Y.; Shin, C. G. Bull. Chem. Soc. Jpn. 1998, 71, 1391.
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A different approach to the nosiheptide core structure has been detailed, (a) Umemura, K.; Noda, H.; Yoshimura, J.; Konn, A.; Yonezawa, Y.; Shin, C. G. Bull. Chem. Soc. Jpn. 1998, 71, 1391.
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54
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34249784697
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See also ref 8b
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(b) See also ref 8b.
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