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28044462470
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note
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One of the reviewers of the manuscript wondered why the free secondary hydroxy group (at C-3) of compound 9, generated during the conversion of 8 → 9, did not undergo further oxidation to the corresponding ketone derivative. A couple of plausible explanations could be as follows: (i) the relatively short reaction time employed for the conversion of 8 → 9 (30 min) could probably be insufficient for carrying out the two-step process of initial cleavage of the silyl protecting group to unmask the hydroxy and subsequent oxidation of this relatively hindered secondary hydroxy to the corresponding ketone. (ii) A second possibility could be an intramolecular hydrogen bond interaction between the favorably placed (and newly generated) carboxylic acid moiety at C-2 and the free hydroxy group at C-3 of compound 9, resulting in the prevention or rate retardation of the oxidation of the hydroxy group. However, additional experiments will have to be carried out to find out the exact reason for the above reaction stopping at product 9.
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