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Kennedy, D.J.1
Selby, I.A.2
Cowe, H.J.3
Cox, P.J.4
Thomson, R.H.5
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2
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0034647232
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For total syntheses of α,α′-trans-oxocene natural products, see: a M. T. Crimmins, E. A. Tabet, J. Am. Chem. Soc. 2000, 122, 5473-5476;
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For total syntheses of α,α′-trans-oxocene natural products, see: a) M. T. Crimmins, E. A. Tabet, J. Am. Chem. Soc. 2000, 122, 5473-5476;
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3
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0036373843
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b) K. Fujiwara, S.-I. Souma, H. Mishima, A. Murai, Synlett 2002, 1493-1495;
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Synlett
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Fujiwara, K.1
Souma, S.-I.2
Mishima, H.3
Murai, A.4
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4
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0037424749
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c) T. Saitoh, T. Suzuki, M. Sugimoto, H. Hagiwara, T. Hoshi, Tetrahedron Lett. 2003, 44, 3175-3178;
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Tetrahedron Lett
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Saitoh, T.1
Suzuki, T.2
Sugimoto, M.3
Hagiwara, H.4
Hoshi, T.5
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5
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33846222902
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d) M. Sugimoto, T. Suzuki, H. Hagiwara, T. Hoshi, Tetrahedron Lett. 2007, 48, 1109-1112;
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Tetrahedron Lett
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Sugimoto, M.1
Suzuki, T.2
Hagiwara, H.3
Hoshi, T.4
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6
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33847637959
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e) H. Kim, H. Lee, D. Lee, S. Kim, D. Kim, J. Am. Chem. Soc. 2007, 129, 2269-2274.
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(2007)
J. Am. Chem. Soc
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Kim, H.1
Lee, H.2
Lee, D.3
Kim, S.4
Kim, D.5
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9
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34347246546
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c) H. M. Sheldrake, C. Jamieson, J. W. Burton, Angew. Chem. 2006, 118, 7357-7360;
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(2006)
Angew. Chem
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Sheldrake, H.M.1
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10
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33751003265
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Angew. Chem. Int. Ed. 2006, 45, 7199-7202.
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(2006)
Chem. Int. Ed
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Angew1
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11
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25444450831
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a) S. D. Lepore, A. K. Bhunia, P. Cohn, J. Org. Chem. 2005, 70, 8117-8121;
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(2005)
J. Org. Chem
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, pp. 8117-8121
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Lepore, S.D.1
Bhunia, A.K.2
Cohn, P.3
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12
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33645755358
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and references therein
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b) S. D. Lepore, A. K. Bhunia, D. Mondal, P. C. Cohn, C. Lefkowitz, J. Org. Chem. 2006, 71, 3285-3286, and references therein.
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(2006)
J. Org. Chem
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, pp. 3285-3286
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Lepore, S.D.1
Bhunia, A.K.2
Mondal, D.3
Cohn, P.C.4
Lefkowitz, C.5
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13
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0033515858
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a) N. Hori, H. Matsukura, G. Matsuo, T. Nakata, Tetrahedron Lett. 1999, 40, 2811-2814;
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(1999)
Tetrahedron Lett
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, pp. 2811-2814
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Hori, N.1
Matsukura, H.2
Matsuo, G.3
Nakata, T.4
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15
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27444447985
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a) H. Lee, H. Kim, T. Yoon, B. Kim, S. Kim, H. Kim, D. Kim, J. Org. Chem. 2005, 70, 8723-8729;
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(2005)
J. Org. Chem
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Lee, H.1
Kim, H.2
Yoon, T.3
Kim, B.4
Kim, S.5
Kim, H.6
Kim, D.7
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16
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34347241939
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in the case of 5′a, the enantiomer of the compound actually prepared is shown for comparison purposes.
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b) in the case of 5′a, the enantiomer of the compound actually prepared is shown for comparison purposes.
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17
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3342898271
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I. Kadota, H. Uyehara, Y. Yamamoto, Tetrahedron 2004, 60, 7361-7365.
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(2004)
Tetrahedron
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Kadota, I.1
Uyehara, H.2
Yamamoto, Y.3
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18
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0000192963
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Y. Oikawa, T. Yoshioka, O. Yonemitsu, Tetrahedron Lett. 1982, 23, 885-888.
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(1982)
Tetrahedron Lett
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Oikawa, Y.1
Yoshioka, T.2
Yonemitsu, O.3
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20
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1542763298
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b) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452;
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Acc. Chem. Res
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Grubbs, R.H.1
Miller, S.J.2
Fu, G.C.3
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21
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34347251426
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for the synthesis of α,α′-trans-oxocene natural products by RCM, see ref. [2a,b].
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c) for the synthesis of α,α′-trans-oxocene natural products by RCM, see ref. [2a,b].
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24
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34347225413
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To the best of our knowledge, this pyranoannulation constitutes the first example of the use of the protocol of Nakata and coworkers for the synthesis of a cis-fused bicyclic structure.
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To the best of our knowledge, this pyranoannulation constitutes the first example of the use of the protocol of Nakata and coworkers for the synthesis of a cis-fused bicyclic structure.
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26
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34347247894
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the free hydroxy group at C12 in 2 was found to be necessary for the efficient chemoselective reduction of the ester functionality in the presence of the α-alkoxy amide group, possibly by internal delivery of the hydride.
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b) the free hydroxy group at C12 in 2 was found to be necessary for the efficient chemoselective reduction of the ester functionality in the presence of the α-alkoxy amide group, possibly by internal delivery of the hydride.
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27
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0000519465
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4NBr in xylene at reflux according to the double-inversion protocol of Masamune and co-workers produced the corresponding bromide in only moderate (20 %) yield as a 2:1 mixture of α and β isomers, along with a significant amount of elimination products: a) A. Fukuzawa, H. Sato, T. Masamune, Tetrahedron Lett. 1987, 28, 4303-4306;
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4NBr in xylene at reflux according to the double-inversion protocol of Masamune and co-workers produced the corresponding bromide in only moderate (20 %) yield as a 2:1 mixture of α and β isomers, along with a significant amount of elimination products: a) A. Fukuzawa, H. Sato, T. Masamune, Tetrahedron Lett. 1987, 28, 4303-4306;
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29
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33847800152
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P. A. Grieco, S. Gilman, M. Nishizawa, J. Org. Chem. 1976, 41, 1485-1486.
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(1976)
J. Org. Chem
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Grieco, P.A.1
Gilman, S.2
Nishizawa, M.3
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30
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0042931243
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H. Kim, W. J. Choi, J. Jung, S. Kim, D. Kim, J. Am. Chem. Soc. 2003, 125, 10238-10240.
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(2003)
J. Am. Chem. Soc
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, pp. 10238-10240
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Kim, H.1
Choi, W.J.2
Jung, J.3
Kim, S.4
Kim, D.5
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34
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0001125915
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a) N. G. Anderson, D. A. Lust, K. A. Colapret, J. H. Simpson, M.F. Malley, J. Z. Gougoutas, J. Org. Chem. 1996, 61, 7955-7958;
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J. Org. Chem
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Anderson, N.G.1
Lust, D.A.2
Colapret, K.A.3
Simpson, J.H.4
Malley, M.F.5
Gougoutas, J.Z.6
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36
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34347211254
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to the best of our knowledge, this reaction is the first example of trisylation under Mitsunobu conditions
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c) to the best of our knowledge, this reaction is the first example of trisylation under Mitsunobu conditions.
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37
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0003066306
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a) C. J. Elsevier, P. Vermeer, A. Gedanken, W. Runge, J. Org. Chem. 1985, 50, 364-367;
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(1985)
J. Org. Chem
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Elsevier, C.J.1
Vermeer, P.2
Gedanken, A.3
Runge, W.4
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38
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3743122078
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b) H. H. Mooiweer, C. J. Elsevier, P. Wijkens, P. Vermeer, Tetrahedron Lett. 1985, 26, 65-66;
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(1985)
Tetrahedron Lett
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Mooiweer, H.H.1
Elsevier, C.J.2
Wijkens, P.3
Vermeer, P.4
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39
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0000687526
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c) T. A. Grese, K. D. Hutchinson, L. E. Overman, J. Org. Chem. 1993, 58, 2468-2477.
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(1993)
J. Org. Chem
, vol.58
, pp. 2468-2477
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Grese, T.A.1
Hutchinson, K.D.2
Overman, L.E.3
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40
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34347258002
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We were unable to obtain the spectra of the natural product from Dr. D. J. Kennedy as a result of his retirement
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We were unable to obtain the spectra of the natural product from Dr. D. J. Kennedy as a result of his retirement.
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41
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34347249776
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Characterization of synthetic 1: Rf, 0.21 (hexane/ethyl acetate, 10:1, m.p. 84-88°C; 1H NMR (500 MHz, CDCl3, δ, 6.11 (1 H, dd, J, 5.9, 2.8 Hz, 1 H, 5.85-6.00 (m, 2 H, 5.81 (ddd, J, 17.2, 10.3,10.3 Hz, 1 H, 5.41-5.45 (m, 2 H, 5.32 (d, J, 10.5 Hz, 1 H, 4.83 (ddd, J, 7.2, 3.5, 3.5 Hz, 1 H, 4.08 (ddd, J, 12.4, 10.1, 4.3 Hz, 1 H, 3.89 (dd, J, 10.2, 6.8 Hz, 1 H, 3.83 (bs, 1 H, 3.69 (dd, J, 9.8, 4.6 Hz, 1 H, 2.65-2.67 (m, 1 H, 2.60 (ddd, J, 12.8, 9.8, 3.0 Hz, 1 H, 2.52 (ddd, J, 7.8, 3.8, 3.8 Hz, 1 H, 2.27-2.33 (m, 2 H, 2.17 ppm (ddd, J, 12.7, 11.5, 3.2 Hz, 1 H, 13C NMR 125 MHz, CDCl3, δ, 202.6, 135.4, 129.3, 128.7, 119.4, 100.0, 83.3, 80.6, 74.9, 74.4, 69.9, 48.0, 43.2, 31.7, 30.2 ppm
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3): δ = 202.6, 135.4, 129.3, 128.7, 119.4, 100.0, 83.3, 80.6, 74.9, 74.4, 69.9, 48.0, 43.2, 31.7, 30.2 ppm.
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