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Examples of these include β-hydroxy-δ-lactones that are pharmacophores of LDL cholesterol-lowering statin drugs (e.g., Lovastatin, Merck: Mevacor), (7a) and oncorhyncolide. (7b)
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Examples of these include β-hydroxy-δ-lactones that are pharmacophores of LDL cholesterol-lowering statin drugs (e.g., Lovastatin, Merck: Mevacor), (7a) and oncorhyncolide. (7b) Clive, D. L. J.; Murthy, K. S. K.; Wee, A. G. H.; Prasad, J. S.; Silva, G. V. J.; Majewski, M.; Anderson, P. C.; Evans, C. F.; Haugen, R. D.; Heerze, L. D.; Barrie, J. R. J. Am. Chem. Soc. 1990, 112, 3018
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For a similar reaction with non-fluorinated β-hydroxy carbonyls, see: Sabitha, G.; Sudhakar, K.; Yadav, J. S. Tetrahedron Lett. 2006, 47, 8599
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0000665529
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Similar low yields have been reported for the methylenation of a β-acetoxy ketone during Wittig reaction
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79952581692
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note
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Attempts to debenzylate the benzyloxy alcohols 1, prepared via the fluoroallylboration of benzaldehyde bearing electron-withdrawing groups, such as p -fluoro, p -chloro, and p -trifluoromethyl groups, resulted in dehalogenation along with debenzylation forming 2a, 2a, and 2c, respectively. Debenyzlation of the benzyloxy alcohol derived from p -nitrobenzaldehyde resulted in the formation of the corresponding p -amino compound, 3,3-difluoro-4-hydroxy-4-(4- aminophenyl)butan-2-one.
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33
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1442324529
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Otaka, A.; Watanabe, J.; Yukimasa, A.; Watanabe, H.; Kinoshita, T.; Oishi, S.; Tamamura, H.; Fujii, N. J. Org. Chem. 2004, 69, 1634
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Fujii, N.8
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35
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79952606058
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note
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2O = 1/1) to provide δ-lactone 6a as a white solid (35 mg, 69%), mp 112-113 °C.
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