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The separation of lactone or its derivatives (acetylated or benzylated lactone) were not successful with HPLC, but after methylation and reduction, the enantiomers of 12 were separable (Daicel AS column, 10% IPA-hexane, 0.5 mL/min, λ = 254 nm, retention times: 29 min and 39 min) and the ee was checked at this point.
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3042699424
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note
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3, Z = 2, 278 parameters, R1 = 0.0405, wR2 = 0.0838. CCDC 212408 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21 EZ, UK; fax: +44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk).
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33748645648
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A similar rearrangement of a ketal to a more stable one occurred in the total synthesis of calyculin A: Tanimoto, N.; Gerritz, S. W.; Sawabe, A.; Noda, T.; Filla, S. A.; Masamune, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 673.
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