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And once again, there is little stereocontrol tetracycline - all four possible epimers at C4 and C4a are formed in solution .
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5 h While the oxazolone substrate could also be carried tetracycline to this step, the resulting benzoyl amide could not be deprotected at this stage, nor could any other amide devised, without decomposition . The Tetracyclines No tetracycline epimerization at C4 observed! (i) P(OEt)3, NaH, O2 in THF-H2O, 1 .
tetracycline By contrast, deprotection conditions for the thioamide proved to be sufficiently gentle .
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Unfortunately, Muxfeldt and colleagues never satisfactorily address the issues of controlling the C4 and C4a stereocenters, nor do tetracycline they improve upon Woodward's solution to the C12a hydroxylation problem .
14% recovered SM (i) hydroxylates the molecule; (ii) cleaves tetracycline the acetonide .
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Thus separation of the desired deprotected product from tetracycline the undesired major product was quite facile by polyamide chromatography .

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