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(b) For other leading references, see ref 4.
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For example, see the following. Kinase inhibitors: Smithkline Beecham, WO 2004043379, 2004. Histamine H3 receptor antagonists: Eli Lilly, WO 2004026837, 2004. 2,3-Oxidosqualene-lanosterol cyclase inhibitors: Hoffmann-La Roche, WO 2002050041, 2002. Growth hormone release promoters: Sumimoto Pharmaceuticals, JP 11292894, 1999. Treatment for dementia: U.S. Department of Health and Human Services, WO 2002048150, 2002. Dopamine D4 receptors: H. Lundbeck A/S, WO 9828293, 1998. Estrogen receptor modulators: Eli Lilly, WO 2002094788, 2002.
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Reported experimental procedure did not work in our hands. However, we were able to make 4.2 (75%) by a modified workup, while a modified method gave 92% yield: PhIO was added to a solution of 4.1 and then TsOH was added. The mixture was concentrated to a small volume (not to dryness) and then chromatographed over silica gel, using MeOH-EtOAc-hexane (the presence of MeOH was essential).
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Oxidation of 4.1 was examined as a model for 33.
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12344273731
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Toluene solutions of tributyltin hydride (0.07-0.12 M) and AIBN (0.005-0.0110 M, 0.1 equiv) were added over 3-5 h to a hot (85°C) solution (0.035 M) of the substrate, and heating was continued for an arbitrary period of 1-10 h after the addition.
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In the absence of molecular sieves, with compound 11b, we did observe the undesired pathway as a minor pathway (we have not tested other compounds under the same conditions or attempted to optimize this minor pathway). Conversion of 14b to 14c was arbitrarily done without molecular sieves.
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