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3] mevalonate in Ginkgo biloba cell cultures: (a) Schwarz, M.; Arigoni, D. In Isoprenoids Including Carotenoids and Steroids: Cane, D. E., Ed.; Vol. 2 in Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Chapter 14.
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Schwarz, M.1
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Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, Chapter 14
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Dissertation 10951, ETH Zürich, Switzerland
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(b) Schwarz, M. K. Dissertation 10951, ETH Zürich, Switzerland, 1994.
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Schwarz, M.K.1
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14
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85085718506
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note
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4, NMO, acetone; 3:1 mixture of 8,17-and 13,-14-diols (78%);
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15
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85085719124
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note
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4 for 6b), ether;
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16
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85085718532
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note
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4, aqueous acetone (60% for two steps).
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17
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85085720390
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note
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13C NMR spectra. Detailed experimental procedures and characterization data are provided in the Supporting Information. Key data are presented in the text or in footnote 14.
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18
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85085719369
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note
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1H NMR δ 5.37 and 6.04 (2d, J = 17.4 Hz, 1H each, CH=CHD).
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33845374468
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For leading references, see: (a) Davisson, V. J.; Woodside, A. B.; Neal, T. R.; Stremler, K. E.; Muehlbacher, M.; Poulter, C. D. J. Org. Chem. 1986, 51, 4768.
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0000481337
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(b) Woodside, A. B.; Huang, Z.; Poulter, C. D. Org. Synth., Coll. Vol. VIII, 1993, 616.
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85085719637
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note
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1H NMR estimate.
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24
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0001318323
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(b) Midland, M. M.; Greer, S.; Tramantano, A.; Zderic, S. A. J. Am. Chem. Soc. 1979, 101, 2352.
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0001211509
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(a) MacMillan, J.; Beale, M. H. In Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Vol. 2 in Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Chapter 8
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(a) MacMillan, J.; Beale, M. H. In Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Vol. 2 in Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Chapter 8
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Comprehensive Natural Products Chemistry
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85085718925
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note
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3H] acetate were kindly provided by H. G. Floss and S. Lee, University of Washington, Seattle, WA. The F values obtained for the chiral acetate standards at the UI were as follows: R, 78.0 ± 3.6; S, 28.1 ± 3.6.
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36
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85085718500
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note
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+ with a 14α deuterium substituent.
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39
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85085718233
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note
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- to form a freely exchangeable covalent diphosphate intermediate appears to be excluded.
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40
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0041289630
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(a) Wise, M. L.; Croteau, R. In Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Vol. 2 in Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier; Oxford, 1999; Chapter 5.
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(a) Wise, M. L.; Croteau, R. In Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Vol. 2 in Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier; Oxford, 1999; Chapter 5.
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(b) Cane, D. E. In Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Vol. 2 in Comprehensive Natural Products Chemists; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Chapter 6.
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(c) Abe, I.; Prestwich, G. D. In Isoprenoids Including Carotenoids and Steroids; Cane, D. E., Ed.; Vol. 2 in Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Chapter 10.
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