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1
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13844306055
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Recent reviews: a
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Recent reviews: (a) Bagley, M. C.; Dale, J. W.; Merritt, E. A.; Xiong, X. Chem. Rev. 2005, 105, 685.
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(2005)
Chem. Rev
, vol.105
, pp. 685
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Bagley, M.C.1
Dale, J.W.2
Merritt, E.A.3
Xiong, X.4
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2
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35648951171
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(b) Hughes, R. A.; Moody, C. J. Angew. Chem., Int. Ed. 2007, 46, 7930.
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(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 7930
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Hughes, R.A.1
Moody, C.J.2
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3
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68049099605
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Major synthetic achievements. Promothiocin A: (a) Moody, C. J.; Bagley, M. C. Chem. Commun. 1998, 2049.
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Major synthetic achievements. Promothiocin A: (a) Moody, C. J.; Bagley, M. C. Chem. Commun. 1998, 2049.
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4
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0034639905
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(b) Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J. J. Am. Chem. Soc. 2000, 122, 3301.
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(2000)
J. Am. Chem. Soc
, vol.122
, pp. 3301
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Bagley, M.C.1
Bashford, K.E.2
Hesketh, C.L.3
Moody, C.J.4
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5
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27644574520
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Amythiamycin D: (c) Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Moody, C. J. J. Am. Chem. Soc. 2005, 127, 15644.
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Amythiamycin D: (c) Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Moody, C. J. J. Am. Chem. Soc. 2005, 127, 15644.
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6
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2442446949
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(d) Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Moody, C. J. Chem. Commun. 2004, 946.
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(2004)
Chem. Commun
, pp. 946
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Hughes, R.A.1
Thompson, S.P.2
Alcaraz, L.3
Moody, C.J.4
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7
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23744471989
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Thiostrepton: (e) Nicolaou, K. C.; Safina, B. S.; Zak, M.; Lee, S. H.; Nevalainen, M.; Bella, M.; Estrada, A. A.; Funke, C.; Zecri, F. J.; Bulat, S. J. Am. Chem. Soc. 2005, 127, 11159.
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Thiostrepton: (e) Nicolaou, K. C.; Safina, B. S.; Zak, M.; Lee, S. H.; Nevalainen, M.; Bella, M.; Estrada, A. A.; Funke, C.; Zecri, F. J.; Bulat, S. J. Am. Chem. Soc. 2005, 127, 11159.
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8
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23744439852
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(f) Nicolaou, K. C.; Zak, M.; Safina, B. S.; Estrada, A. A.; Lee, S. H.; Nevalainen, M. J. Am. Chem. Soc. 2005, 127, 11176.
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(2005)
J. Am. Chem. Soc
, vol.127
, pp. 11176
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Nicolaou, K.C.1
Zak, M.2
Safina, B.S.3
Estrada, A.A.4
Lee, S.H.5
Nevalainen, M.6
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9
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4944238016
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(g) Nicolaou, K. C.; Safina, B. S.; Zak, M.; Estrada, A. A.; Lee, S. H. Angew. Chem., Int. Ed. 2004, 43, 5087.
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(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 5087
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Nicolaou, K.C.1
Safina, B.S.2
Zak, M.3
Estrada, A.A.4
Lee, S.H.5
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10
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4944267509
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(h) Nicolaou, K. C.; Zak, M.; Safina, B. S.; Lee, S. H.; Estrada, A. A. Angew. Chem., Int. Ed. 2004, 43, 5092.
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(2004)
Angew. Chem., Int. Ed
, vol.43
, pp. 5092
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Nicolaou, K.C.1
Zak, M.2
Safina, B.S.3
Lee, S.H.4
Estrada, A.A.5
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11
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33846350838
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Siomycin A: (i) Mori, T.; Higashibayashi, S.; Goto, T.; Kohno, M.; Satouchi, Y.; Shinko, K.; Suzuki, K.; Suzuki, S.; Tohmiya, H.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2007, 48, 1331.
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Siomycin A: (i) Mori, T.; Higashibayashi, S.; Goto, T.; Kohno, M.; Satouchi, Y.; Shinko, K.; Suzuki, K.; Suzuki, S.; Tohmiya, H.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2007, 48, 1331.
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12
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33845290273
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GE2270A and GE 2270T: (j) Nicolaou, K. C, Zou, B, Dethe, D. H, Li, D. B, Chen, D. Y. K. Angew. Chem, Int. Ed. 2006, 45, 7786
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GE2270A and GE 2270T: (j) Nicolaou, K. C.; Zou, B.; Dethe, D. H.; Li, D. B.; Chen, D. Y. K. Angew. Chem., Int. Ed. 2006, 45, 7786.
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13
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34347213763
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(k) Muller, H. M.; Delgado, O.; Bach, T. Angew. Chem., Int. Ed. 2007, 46, 4771.
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(2007)
Angew. Chem., Int. Ed
, vol.46
, pp. 4771
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Muller, H.M.1
Delgado, O.2
Bach, T.3
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14
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53849105812
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(l) Delgado, O.; Muller, H. M.; Bach, T. Chem. - Eur. J. 2008, 14, 2322.
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(2008)
Chem. - Eur. J
, vol.14
, pp. 2322
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Delgado, O.1
Muller, H.M.2
Bach, T.3
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15
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70349786238
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Micrococcin P1: (m) Lefranc, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2009, 48, 4198.
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Micrococcin P1: (m) Lefranc, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2009, 48, 4198.
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16
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0037014040
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(a) Nicolaou, K. C.; Nevalainen, M.; Safina, B. S.; Zak, M.; Bulat, S. Angew. Chem., Int. Ed. 2002, 41, 1941.
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(2002)
Angew. Chem., Int. Ed
, vol.41
, pp. 1941
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Nicolaou, K.C.1
Nevalainen, M.2
Safina, B.S.3
Zak, M.4
Bulat, S.5
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17
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0036056973
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Moody, C. J; Hughes, R. A.; Thompson, S. P.; Alcaraz, L. Chem. Commun. 2002, 1760. See also ref 2d.
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(b) Moody, C. J; Hughes, R. A.; Thompson, S. P.; Alcaraz, L. Chem. Commun. 2002, 1760. See also ref 2d.
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18
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68049092397
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Noteworthy in this regard is the Bach approach refs 2k and 2l, See ref 1 for a thorough bibliography
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Noteworthy in this regard is the Bach approach (refs 2k and 2l). See ref 1 for a thorough bibliography.
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21
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35348959557
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Moody introduced the reaction into current synthetic practice during his pioneering synthesis of promothiocin A (ref 2a, Review: b
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Review: (b) Bagley, M. C.; Glover, C.; Merritt, E. A. Synlett 2007, 2459. Moody introduced the reaction into current synthetic practice during his pioneering synthesis of promothiocin A (ref 2a).
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(2007)
Synlett
, pp. 2459
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Bagley, M.C.1
Glover, C.2
Merritt, E.A.3
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23
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1642540130
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Bagley, M. C.; Dale, J. W.; Jenkins, R. L.; Bower, J. Chem. Commun. 2004, 102.
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(2004)
Chem. Commun
, pp. 102
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Bagley, M.C.1
Dale, J.W.2
Jenkins, R.L.3
Bower, J.4
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24
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68049108737
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For representative methods see the preparation of compounds 7 and 12 (Scheme 2 herein) as described in ref 5 (12, 8 steps from glycolonitrile, 25%), ref 8, and in the following: Merritt, E. A.; Bagley, M. C. Synlett 2007, 954 (7, 4 steps from diethoxyacetonitrile, 83%).
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For representative methods see the preparation of compounds 7 and 12 (Scheme 2 herein) as described in ref 5 (12, 8 steps from glycolonitrile, 25%), ref 8, and in the following: Merritt, E. A.; Bagley, M. C. Synlett 2007, 954 (7, 4 steps from diethoxyacetonitrile, 83%).
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25
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68049098536
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This reaction forms a black precipitate of Se byproducts. Perhaps this precipitate entrains byproducts arising from 11
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This reaction forms a black precipitate of Se byproducts. Perhaps this precipitate entrains byproducts arising from 11.
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26
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68049103525
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The use of IBX for the oxidation of such carbinols was introduced by Moody (refs 2a and 2b). We found that the Dess-Martin periodinane performed better than IBX in the oxidation of 15.
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The use of IBX for the oxidation of such carbinols was introduced by Moody (refs 2a and 2b). We found that the Dess-Martin periodinane performed better than IBX in the oxidation of 15.
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27
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68049089132
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This known compound was made as detailed in the Supporting Information
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This known compound was made as detailed in the Supporting Information.
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28
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13844320099
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(a) Bagley, M. C.; Chapaneri, K.; Dale, J. W.; Xiong, X.; Bower, J. J. Org. Chem. 2005, 70, 1389.
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(2005)
J. Org. Chem
, vol.70
, pp. 1389
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Bagley, M.C.1
Chapaneri, K.2
Dale, J.W.3
Xiong, X.4
Bower, J.5
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0035996944
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See also: b
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See also: (b) Bagley, M. C.; Brace, C.; Dale, J. W.; Ohnesorge, M.; Phillips, N. G.; Xiong, X.; Bower, J. J. Chem. Soc., Perkin Trans. I 2002, 1663.
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(2002)
J. Chem. Soc., Perkin Trans. I
, pp. 1663
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Bagley, M.C.1
Brace, C.2
Dale, J.W.3
Ohnesorge, M.4
Phillips, N.G.5
Xiong, X.6
Bower, J.7
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31
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33644839140
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A similar reaction may be carried out in ionic liquids: Karthikeyan, G.; Perumal, P. T. Can. J. Chem. 2005, 83, 1746.
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A similar reaction may be carried out in ionic liquids: Karthikeyan, G.; Perumal, P. T. Can. J. Chem. 2005, 83, 1746.
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32
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0019806682
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Thiocillin, I.; Shoji, J.; Kato, T.; Yoshimura, Y.; Tori, K. J. Antibiot. 1981, 34, 1126.
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(1981)
J. Antibiot
, vol.34
, pp. 1126
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Thiocillin, I.1
Shoji, J.2
Kato, T.3
Yoshimura, Y.4
Tori, K.5
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33
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0037300530
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YM-266183: Nagai, K, Kamigiri, K, Arao, N, Suzumura, K.-I, Kawano, Y, Yamaoka, M, Zhang, H, Watanabe, M, Suzuki, K. J. Antibiot. 2003, 56, 123
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YM-266183: Nagai, K.; Kamigiri, K.; Arao, N.; Suzumura, K.-I.; Kawano, Y.; Yamaoka, M.; Zhang, H.; Watanabe, M.; Suzuki, K. J. Antibiot. 2003, 56, 123.
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34
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68049112861
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Conduct of the reaction in EtOH again failed to produce pyridines
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Conduct of the reaction in EtOH again failed to produce pyridines.
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35
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68049104581
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Experimental protocols are provided as Supporting Information
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Experimental protocols are provided as Supporting Information.
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36
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68049093425
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Details of the HPLC analysis are provided as Supporting Information
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Details of the HPLC analysis are provided as Supporting Information.
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