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Lactol 33 was formed as a mixture of diastereomers.
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(b) Duan, J. J.-W.; Sprengeler, P. A.; Smith, A. B., III. Tetrahedron Lett. 1992, 33, 6439-6442.
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Tetrahedron Lett.
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Duan, J.J.-W.1
Sprengeler, P.A.2
Smith III, A.B.3
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90
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0025345826
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-
Cyclizations of this type have been referred to as hybrid 6-endo-tet/5-exo-tet by Warren: McIntyre, S.; Warren, S. Tetrahedron Lett. 1990, 31, 3457-3460.
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-
McIntyre, S.1
Warren, S.2
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92
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0344327863
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note
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(a) The relative configuration of 50 could be assigned only after reductive removal of the phenylselenyl moiety by comparison with 52 obtained from iodide 44.
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-
-
-
93
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0344327864
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-
note
-
(b) In the absence of 2,6-di-tert-butyl-4-methylpyridine, deprotection of the C5 silyl ether was observed.
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-
-
-
94
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33845471903
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-
(a) Houk, K. N.; Moses, S. R.; Wu, Y. D.; Rondan, N. G.; Jäger, V.; Schohe, R.; Fronczek, F. R. J. Am. Chem. Soc. 1984, 106, 3880-3882.
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Houk, K.N.1
Moses, S.R.2
Wu, Y.D.3
Rondan, N.G.4
Jäger, V.5
Schohe, R.6
Fronczek, F.R.7
-
96
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-
0036354971
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-
For a review on tin-hydride substitutes in reductive radical chain reactions, see: Studer, A.; Amrein, S. Synthesis 2002, 835-849.
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(2002)
Synthesis
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Studer, A.1
Amrein, S.2
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97
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0034283587
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Studer, A.; Amrein, S.Angew. Chem., Int. Ed. 2000, 39, 3080-3082.
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Studer, A.1
Amrein, S.2
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99
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0001127245
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For a general discussion on the energetics of lactonization, see: Mandolini, L. J. Am. Chem. Soc. 1978, 100, 550-554.
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J. Am. Chem. Soc.
, vol.100
, pp. 550-554
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Mandolini, L.1
-
100
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0344759901
-
-
note
-
Seco acid 54 was prepared from 40 by O-methylation of the C9 hydroxy group, followed by a reaction pathway similar to that described for the conversion of diol 37 to seco acid 56.
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-
-
-
101
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0001616071
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Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
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Inanaga, J.1
Hirata, K.2
Saeki, H.3
Katsuki, T.4
Yamaguchi, M.5
-
102
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-
0345190302
-
-
note
-
Leighton and Rychnovsky have reported similar Yamaguchi macrolactonization reactions with substrates incorporating a C9 methyl ether, giving macrocycles in good yields. See ref 8 and 9.
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-
-
-
103
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0019439350
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-
Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Auyeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H.; Chenevert, R. B.; Fliri, A.; Frobel, K.; Gais, H. J.; Garratt, D. G.; Hayakawa, K.; Heggie, W.; Hesson, D. P.; Hoppe, D.; Hoppe, I.; Hyatt, J. A.; Ikeda, D.; Jacobi, P. A.; Kim, K. S.; Kobuke, Y.; Kojima, K.; Krowicki, K.; Lee, V. J.; Leutert, T.; Malchenko, S.; Martens, J.; Matthews, R. S.; Ong, B. S.; Press, J. B.; Babu, T. V. R.; Rousseau, G.; Sauter, H. M.; Suzuki, M.; Tatsuta, K.; Tolbert, L. M.; Truesdale, E. A.; Uchida, I.; Ueda, Y.; Uyehara, T.; Vasella, A. T.; Vladuchick, W. C.; Wade, P. A.; Williams, R. M.; Wong, H. N. C. J. Am. Chem. Soc. 1981, 103, 3213-3215.
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Woodward, R.B.1
Logusch, E.2
Nambiar, K.P.3
Sakan, K.4
Ward, D.E.5
Auyeung, B.W.6
Balaram, P.7
Browne, L.J.8
Card, P.J.9
Chen, C.H.10
Chenevert, R.B.11
Fliri, A.12
Frobel, K.13
Gais, H.J.14
Garratt, D.G.15
Hayakawa, K.16
Heggie, W.17
Hesson, D.P.18
Hoppe, D.19
Hoppe, I.20
Hyatt, J.A.21
Ikeda, D.22
Jacobi, P.A.23
Kim, K.S.24
Kobuke, Y.25
Kojima, K.26
Krowicki, K.27
Lee, V.J.28
Leutert, T.29
Malchenko, S.30
Martens, J.31
Matthews, R.S.32
Ong, B.S.33
Press, J.B.34
Babu, T.V.R.35
Rousseau, G.36
Sauter, H.M.37
Suzuki, M.38
Tatsuta, K.39
Tolbert, L.M.40
Truesdale, E.A.41
Uchida, I.42
Ueda, Y.43
Uyehara, T.44
Vasella, A.T.45
Vladuchick, W.C.46
Wade, P.A.47
Williams, R.M.48
Wong, H.N.C.49
more..
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104
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0345190299
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note
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1H NMR.
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-
-
-
105
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0030750871
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(a) Ireland, R. E.; Liu, L. B.; Roper, T. D.; Gleason, J. L. Tetrahedron 1997, 53, 13257-13284.
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Tetrahedron
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Ireland, R.E.1
Liu, L.B.2
Roper, T.D.3
Gleason, J.L.4
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106
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0028021609
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(b) Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. Tetrahedron Lett. 1994, 35, 7171-7172.
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Tetrahedron Lett.
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Evans, D.A.1
Ratz, A.M.2
Huff, B.E.3
Sheppard, G.S.4
-
107
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0023740262
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Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J. Am. Chem. Soc. 1988, 110, 4672-4685.
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Nicolaou, K.C.1
Daines, R.A.2
Uenishi, J.3
Li, W.S.4
Papahatjis, D.P.5
Chakraborty, T.K.6
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108
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26844568935
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(a) Blakemore, P. R.; Cole, W. J.; Kocieñski, P. J.; Morley, A. Synlett 1998, 26-28.
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(1998)
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Blakemore, P.R.1
Cole, W.J.2
Kocieñski, P.J.3
Morley, A.4
-
110
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0026089935
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(a) Baudin, J. B.; Hareau, G.; Julia, S. A.; Ruel, O. Tetrahedron Lett. 1991, 32, 1175-1178.
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(1991)
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Baudin, J.B.1
Hareau, G.2
Julia, S.A.3
Ruel, O.4
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112
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37049106827
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(c) Kocieñski, P. J.; Lythgoe, B.; Ruston, S. J. Chem. Soc., Perkin Trans. 1 1978, 829-834.
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(1978)
J. Chem. Soc., Perkin Trans. 1
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Kocieñski, P.J.1
Lythgoe, B.2
Ruston, S.3
-
113
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0344759899
-
-
note
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Sulfone 61 was prepared from 3-methyl-1-butanol and commercially available 1-phenyl-5-mercaptotetrazole using the Mitsunobu protocol (86%) followed by oxidation of the resulting sulfide to the corresponding sulfone 61 with oxone in 90% yield.
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