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8
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0034775138
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9
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0024605063
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12
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0000103823
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Gilman H., Beel J.A., Brannen C.G., Bullock M.W., Dunn G.E., Miller L.S. J. Am. Chem. Soc. 71:1949;1499
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14
-
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0013403284
-
-
note
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2O at -78°C and were used directly.
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-
-
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15
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0037170757
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Serrano-Wu M.H., St Laurent D.R., Mazzucco C.E., Stickle T.M., Barrett J.F., Vyas D.M., Balasubramanian B.N. Bioorg. Med. Chem. Lett. 12:2002;943.
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Serrano-Wu, M.H.1
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Mazzucco, C.E.3
Stickle, T.M.4
Barrett, J.F.5
Vyas, D.M.6
Balasubramanian, B.N.7
-
16
-
-
0013459055
-
-
note
-
6, 400 MHz) δ 5.00 (s, 1H), 4.24 (m, 1H), 4.11 (m, 1H), 3.66 (m, 1H), 3.44 (m, 1H), 3.38-3.27 (m, 3H), 3.15 (d, 1H, J=18.4 Hz), 3.09 (s, 1H), 2.06-1.61 (m, 11H), 1.75 (s, 3H), 1.68 (s, 3H), 1.46-1.21 (m, 7H), 0.91 (d, 3H, J=7.1 Hz), -0.14 (s, 9H).
-
-
-
-
18
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0001290261
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Trost, B. M. Ed., Pergamon Press: New York
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Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M. Ed., Pergamon Press: New York, 1991; Vol. 2, p 527.
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Snider, B.B.1
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19
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0013458070
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-
note
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However, upon oxidation of 12 under Swern conditions, the ketone 15 is the only product isolated. Under the proposed Swern oxidation mechanism, the initially formed activated alcohol becomes oxidized upon addition of the base and therefore 14 is formed, even at -78°C. Interestingly, the rate of the following step appears much quicker than with the Dess-Martin reagent as the alcohol 14 is transformed to ketone 15 even at this low temperature before the reagent is destroyed. This dichotomy in the rates for the second step may be due to the greater steric encumbrance of the Dess-Martin periodinane over that of the activated DMSO for the Swern oxidation.
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-
-
-
20
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0013413733
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-
note
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Alternatively, the reaction may be envisioned to proceed via initial acetate (from the Dess-Martin reagent) abstraction of the seemingly non-acidic allylic proton.
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-
-
-
21
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0013407483
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note
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MICs were determined according to NCCLS standards against fungal strains obtained from the American Type Culture Collection.
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-
-
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22
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0032544158
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Tse B., Balkovec J.M., Blazey C.M., Hsu M.J., Nielsen J., Schmatz D. Bioorg. Med. Chem. Lett. 8:1998;2269.
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Tse, B.1
Balkovec, J.M.2
Blazey, C.M.3
Hsu, M.J.4
Nielsen, J.5
Schmatz, D.6
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