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Zeolite NaY was dried and activated as described in ref 12.
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Zeolite NaY was dried and activated as described in ref 12.
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22
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33847782840
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Typical cyclization procedure: 9,10-Epoxygeranylacetone (3b, 200 mg, 0.95 mmol) was adsorbed onto dry zeolite NaY (1 g) that had been previously suspended in hexane (15 mL). The resultant slurry was heated to 70°C for 1 h and then filtered. The solid residue was washed with methanol (2 × 10 mL) for 30 min each time. The combined extracts were evaporated under reduced pressure to afford 184 mg of a mixture containing 4b, 5b, and 6b (see Table 1).
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Typical cyclization procedure: 9,10-Epoxygeranylacetone (3b, 200 mg, 0.95 mmol) was adsorbed onto dry zeolite NaY (1 g) that had been previously suspended in hexane (15 mL). The resultant slurry was heated to 70°C for 1 h and then filtered. The solid residue was washed with methanol (2 × 10 mL) for 30 min each time. The combined extracts were evaporated under reduced pressure to afford 184 mg of a mixture containing 4b, 5b, and 6b (see Table 1).
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3-catalyzed cyclization of 14 gives a complex reaction mixture, with a very low yield of bicyclic hydroxy acetates, without any monocyclization products such as 15 or 16 being formed: van Tamelen, E. E.; Storni, A.; Hessler E. J.; Schwartz, M. A. Bioorg. Chem. 1982, 11, 133-170.
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3-catalyzed cyclization of 14 gives a complex reaction mixture, with a very low yield of bicyclic hydroxy acetates, without any monocyclization products such as 15 or 16 being formed: van Tamelen, E. E.; Storni, A.; Hessler E. J.; Schwartz, M. A. Bioorg. Chem. 1982, 11, 133-170.
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For a typical example, see
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For a typical example, see: Matsuda, S. P. T.; Darr, L. B.; Hart, E. A.; Herrera, J. B. R.; McCann, K. E.; Meyer, M. M.; Pang, J. H.; Schepmann, H. G. Org. Lett. 2000, 2, 2261-2263.
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