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33645033908
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Tedanolide C (1)
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0001156916
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13-Deoxytedanolide (3)
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Candidaspongiolide (4)
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McKee, T.C.11
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6
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77952407547
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Ger. Pat. 2,155,113. For reviews of the Baylis-Hillman reacdtion, see
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Baylis, A.B.1
Hillman, M.E.D.2
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Ma, G.-N.1
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11
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77952328433
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For reports of enantioselective Baylis-Hillman reactions with chiral acylate derivatives
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For reports of enantioselective Baylis-Hillman reactions with chiral acylate derivatives
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12
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0031004738
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references cited therein
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Brzezinski, L. J.; Rafel, S.; Leahy, J. W. J. Am. Chem. Soc. 1997, 119, 4317 and references cited therein
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14
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77952385891
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note
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For previous syntheses of racemic Baylis-Hillman adducts from aldol reactions of β-selenophenyl enolboranes see
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17
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0012016624
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Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127
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24
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77952388703
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note
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4 gave a mixture of the 1,2- and the 1,4-reduced products in a 1:1 ratio.
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28
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4444276636
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Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483
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Kolb, H.C.1
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29
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77952328918
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note
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The stereochemistry of the C(16) hydroxy group was assigned based on the usual sense of asymmetric induction in Sharpless asymmetric dihydroxylation reactions, and was not rigorously determined at this stage.
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30
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77952346243
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note
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The two diastereomers were inseparable by standard column chromatography. Purification of the major diastereomer was performed by HPLC.
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