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Reference 4 originally reported the total synthesis of naturally occurring tubulysins U and V, but was actually the synthesis of epimeric compounds. Correction: Dömling, A.; Beck, B.; Eichelberger, U.; Sakamuri, S.; Menon, S.; Chen, Q.-Z.; Lu, Y.; Wessjohann, L. A. Angew. Chem., Int. Ed. 2007, 46, 2337-2348.
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Other cancer cell lines such as human cervix carcinoma KB-3-1 (DSMZ ACC 158) and mouse fibroblast L929 (DSMZ ACC 2) also showed comparable biological activities.
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Other cancer cell lines such as human cervix carcinoma KB-3-1 (DSMZ ACC 158) and mouse fibroblast L929 (DSMZ ACC 2) also showed comparable biological activities.
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45249107822
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For an alternative synthesis of 2, see ref 7
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For an alternative synthesis of 2, see ref 7.
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45249118453
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Prepared as described in ref 12 in three steps from phenylacetaldehyde
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Prepared as described in ref 12 in three steps from phenylacetaldehyde.
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To our knowledge no examples exist of reducing 1,3-N-acyl-, 1,3-N-sulfonyl-, or 1,3-N-sulfinyl-tetrahydrooxazines to the corresponding 1,3-amino alcohol. For examples with 1,2-N-acyl- oxazolidines, see refs 25f, i, and 25j, as well as: (a) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Chem. Commun. 1999, 4, 317-318.
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Facile O- to N-acyl transfer has been reported, most notably in the N-methyl-1,2-amino alcohol pseudoephedrine series. See ref 29 and: (a) Myers, A. G, Gleason, J. L, Yoon, T, Kung, D. W J. Am. Chem. Soc. 1997, 119, 656-673
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55
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Due to the unprotected carboxylic acid present in 22, PFP-ester activation was used in preference to carbodiimide coupling procedures that would cause oligomerization.
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Due to the unprotected carboxylic acid present in 22, PFP-ester activation was used in preference to carbodiimide coupling procedures that would cause oligomerization.
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