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In the course of studying its mode of action, analogues with less degree of N-methylation were synthesized. Thus, considerable attention has received the desmethylated triostin A TANDEM, T. L. Ciardelli, R. K. Olsen, J. Am. Chem. Soc. 1977, 99, 2806-2807
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In the course of studying its mode of action, analogues with less degree of N-methylation were synthesized. Thus, considerable attention has received the desmethylated triostin A (TANDEM), [T. L. Ciardelli, R. K. Olsen, J. Am. Chem. Soc. 1977, 99, 2806-2807]
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and modifications on it such as the bis L-Ser TANDEM [T. L. Ciardelli, P. K. Chakravarty, R. K. Olsen, J. Am. Chem. Soc. 1978, 100, 7684-7690]
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Furthermore, an increase in conformational rigidity has been shown by the aza analogue of triostin A, azatriostin [D. L. Boger, J. K. Lee, J. Org. Chem. 2000, 65, 5996-6000]. All these synthesis had been carried in solution.
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Syntheses on the solid-phase have been limited up to now to the desmethylated analogue of triostin (TANDEM) and to its aza derivative: a) J. P. Malkinson, M. K. Anim, M. Zloh, M. Searcey, J. Org. Chem. 2005, 70, 7654-7661;
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Syntheses on the solid-phase have been limited up to now to the desmethylated analogue of triostin (TANDEM) and to its aza derivative: a) J. P. Malkinson, M. K. Anim, M. Zloh, M. Searcey, J. Org. Chem. 2005, 70, 7654-7661;
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Previous studies on N-methylated analogues had shown that the ester bond between the NMe-Val and the D-Ser was not stable to piperidine
-
Previous studies on N-methylated analogues had shown that the ester bond between the NMe-Val and the D-Ser was not stable to piperidine.
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35
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54349125520
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Kociénsky [P. J. Kociénsky, Protecting groups, 3rd edition, Thieme, Stuttgart (Germany), 2004, pp. 29-32] describes several examples showing that a conformation change can produce new hindrance resulting in a modification of the regioselectivity or the stereospecificity, but to the best of our knowledge this is the first example of the new concept of protection.
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Kociénsky [P. J. Kociénsky, Protecting groups, 3rd edition, Thieme, Stuttgart (Germany), 2004, pp. 29-32] describes several examples showing that a conformation change can produce new hindrance resulting in a modification of the regioselectivity or the stereospecificity, but to the best of our knowledge this is the first example of the new concept of protection.
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Personal communication.
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