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0043097578
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A small portion of these studies were disclosed in a 1996 presentation; see: Kamenecka, T. M.; Ly, S. K.; Overman, L. E. Abstracts of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL.; American Chemical Society: Washington, DC, 1996: ORGN 010.
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0000975755
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For other sequential reactions that are initiated by conjugate reduction with Stryker's reagent, see: (a) Chiu, P.; Szeto, C.-P.; Geng, Z.; Cheng, K.-F. Org. Lett. 2001, 3, 1901-1903.
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(b) Lipshutz, B. H.; Chrisman, W.; Noson, K.; Papa, P.; Sclafani, J. A.; Vivian, R. W.; Keith, J. M. Tetrahedron 2000, 56, 2779-2788.
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(c) Chiu, P.; Chen, B.; Cheng, K.-F. Tetrahedron Lett. 1998, 39, 9229-9232.
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(d) Kiyooka, S.; Shimizu, A.; Torii, S. Tetrahedron Lett. 1998, 39, 5237-5240.
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29
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0042596719
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ref 5a
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(e) ref 5a.
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31
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0010401364
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(b) Altenbach, H.-J.; Holzapfel, W.; Smerat, G.; Finkler, S. H. Tetrahedron Lett. 1985, 26, 6329-6332.
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33845373603
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(b) Z isomer: Takai, K.; Nitta, K.; Utimoto, K. J. Am. Chem. Soc. 1986, 108, 7408-7410.
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36
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0042596720
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-
note
-
3P can be removed from 5 by slurrying the reagent with hexane or benzene under an argon or nitrogen atmosphere and filtering and drying residual 5 under vacuum.
-
-
-
-
37
-
-
0042095713
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-
note
-
The high stereoselectivity seen in toluene in reductive silylation of 8a with Stryker's reagent suggests the use of this reagent and solvent for stereocontrolled synthesis of other acyclic (Z)-enoxysilanes.
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-
-
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38
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0013487871
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Diagnostic chemical shifts of the C8 vinylic hydrogens of (Z)- and (E)-15 readily defined their configurations; see: Saunders, W. H.; Xie, L. F. J. Am. Chem. Soc. 1991, 113, 3123-3130.
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39
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0043097574
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0042095712
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Ly, S. K. Ph.D. Dissertation, University of California, Irvine, CA, 1998.
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Ly, S.K.1
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0042095705
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Kamenecka, T. M. Ph.D. Dissertation, University of California, Irvine, CA, 1996.
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Kamenecka, T.M.1
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0008006132
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Available in one step and high yield from dimethyl glutarate; see: Wenkert, E.; Schorp, M. K. J. Org. Chem. 1994, 59, 1943-1944.
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46
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0041594746
-
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note
-
13C NMR spectra of crude reaction products.
-
-
-
-
47
-
-
0042596718
-
-
note
-
That epimerization of the carboxyl substituent did not occur under the basic hydrolysis conditions was confirmed by reaction of acid 36 with diazomethane to return 32.
-
-
-
-
48
-
-
0041594738
-
-
note
-
3P, cyclization of 8b by the conditions reported in Scheme 3 gave 13b and 14b in a 1:1 ratio.
-
-
-
-
49
-
-
0042596717
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-
note
-
26 As a result of destabilizing steric interactions between C5 and a Z ester group, (Z)-enoate 9 should also have a reduced propensity to cyclize in the fashion depicted in Figure 1.
-
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50
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33751157924
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