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33744935763
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For a lead reference concerning syntheses of 2,6-disubstituted tetrahydropyrans, see
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a) For a lead reference concerning syntheses of 2,6-disubstituted tetrahydropyrans, see: N. Kawai, J.-M. Lagrange, M. Ohmi, J. Uenishi, J. Org. Chem. 2006, 71, 4530-4537;
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For an example of an intramolecular hetero-Michael addition to a hydroxybutenolide for construction of a pyrano-γ-lactone, see: G. A. Kraus, B. Roth, J. Org. Chem. 1978, 43, 4923-4924
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For an example of an intramolecular hetero-Michael addition to a hydroxybutenolide for construction of a pyrano-γ-lactone, see: G. A. Kraus, B. Roth, J. Org. Chem. 1978, 43, 4923-4924.
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33751003265
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and references therein;
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Angew. Chem. Int. Ed. 2006, 45, 7199-7202, and references therein;
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b) J. Park, B. Kim, H. Kim, S. Kim, D. Kim, Angew. Chem. 2007, 119, 4810-4812;
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85083243520
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For reviews of the Wacker oxidation, see: a
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For reviews of the Wacker oxidation, see: a) J. Tsuji, Synthesis 1984, 369-384;
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Tsuji, J.1
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0000508605
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For the aldehyde-selective Wacker oxidation of allylic diol derivatives, see
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For the aldehyde-selective Wacker oxidation of allylic diol derivatives, see: S.-K. Kang, K.-Y. Jung, J.-U. Chung, E.-Y. Namkoong, T.-H. Kim, J. Org. Chem. 1995, 60, 4678-4679.
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21
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53549088694
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-
It is interesting to note that the Wacker oxidation of the C12/C13-anti isomer under comparable conditions gave the corresponding ketone as the major regioisomer; see the Supporting Information.
-
It is interesting to note that the Wacker oxidation of the C12/C13-anti isomer under comparable conditions gave the corresponding ketone as the major regioisomer; see the Supporting Information.
-
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22
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0000192963
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Y. Oikawa, T. Yochika, O. Yonemitsu, Tetrahedron Lett. 1982, 23, 885-888.
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53549092596
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CCDC-656345 (for 2), CCDC-667564 (for ent-3a), and CCDC-656346 (for 4b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif; see also the Supporting Information.
-
CCDC-656345 (for 2), CCDC-667564 (for ent-3a), and CCDC-656346 (for 4b) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif; see also the Supporting Information.
-
-
-
-
24
-
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33751157732
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-1, respectively.
-
-1, respectively.
-
-
-
-
25
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53549112275
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-
Separation of the 10R and 10S isomers and subjection of each isomer to the IHMA conditions gave roughly the same result. b The minor α,α′-cis isomer 3b did not equilibrate to the corresponding trans isomer 3a under the reaction conditions.
-
a) Separation of the 10R and 10S isomers and subjection of each isomer to the IHMA conditions gave roughly the same result. b) The minor α,α′-cis isomer 3b did not equilibrate to the corresponding trans isomer 3a under the reaction conditions.
-
-
-
-
26
-
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53549123363
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Independently synthesized 3′a equilibrated completely to 3′b after 80 h under the reaction conditions (≈ 30% after 24 h).
-
Independently synthesized 3′a equilibrated completely to 3′b after 80 h under the reaction conditions (≈ 30% after 24 h).
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-
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27
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33947473632
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a) F. Ramirez, N. B. Desai, N. McKelvie, J. Am. Chem. Soc. 1962, 84, 1745-1747;
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0013601019
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b) R. Mahrwald, F. Theil, H. Schick, H.-J. Palme, H. Nowak, G. Weber, S. Schwarz, Synthesis 1987, 1012-1013, and references therein;
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Mahrwald, R.1
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Schwarz, S.7
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33
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53549116000
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2 bromination of C13-ethyl, -vinyl, -(Z)-1-bromovinyl, -(E)-1-bromovinyl, and -1,1-dibromovinyl groups were 17, 13, 53, 10, and 77%, respectively.
-
2 bromination of C13-ethyl, -vinyl, -(Z)-1-bromovinyl, -(E)-1-bromovinyl, and -1,1-dibromovinyl groups were 17, 13, 53, 10, and 77%, respectively.
-
-
-
-
34
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84982069593
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a) L. Horner, H. Oediger, H. Hoffmann, Justus Liebigs Ann. Chem. 1959, 626, 26-34;
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a) A. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 1977, 18, 4171-4172;
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and references therein
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b) T. Shimizu, K. Osako, T. Nakata, Tetrahedron Lett. 1997, 38, 2685-2688, and references therein.
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Shimizu, T.1
Osako, K.2
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39
-
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53549089693
-
-
protection of the hydroxy group at the C10 position was critical for the success of the Weinreb ketone synthesis.
-
b) protection of the hydroxy group at the C10 position was critical for the success of the Weinreb ketone synthesis.
-
-
-
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40
-
-
33847637959
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-
and references therein
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H. Kim, H. Lee, D. Lee, S. Kim, D. Kim, J. Am. Chem. Soc. 2007, 129, 2269-2274, and references therein.
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