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1
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15644373055
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(a) Dabrah, T. T.; Harwood, H. J.; Huang, L. H.; Jankovich, N. D.; Kaneko, T.; Li, J. C.; Lindsey, S.; Moshier, P. M.; Subashi, T. A.; Therrien, M.; Watts, P. C. J. Antibiot. 1997, 50, 1-7.
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Dabrah, T.T.1
Harwood, H.J.2
Huang, L.H.3
Jankovich, N.D.4
Kaneko, T.5
Li, J.C.6
Lindsey, S.7
Moshier, P.M.8
Subashi, T.A.9
Therrien, M.10
Watts, P.C.J.11
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2
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0030948407
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(b) Dabrah, T. T.; Kaneko, T.; Massefski, W.; Whipple, E. B. J. Am. Chem. Soc. 1997, 119, 1594-1598.
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Dabrah, T.T.1
Kaneko, T.2
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Whipple, E.B.4
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3
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0028841895
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and references cited within
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Bergstrom, J. D.; Dufresne, C.; Bills, G. F.; Nallin-Omstead, M.; Byrne, K. Annu. Rev. Microbiol. 1995, 49, 607-639 and references cited within.
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Bergstrom, J.D.1
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Nallin-Omstead, M.4
Byrne, K.5
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4
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0342389956
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note
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We have tentatively assigned the fungus to the Ascomycete order Pleosporales based on ITS sequence. Unpublished results by Nancy P. Keller, Paul Spencer, and Gary A. Sulikowski.
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-
-
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5
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0033153049
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Total Synthesis: (a) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Choi, H. S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem., Int. Ed. Engl. 1999, 38, 1669-1675. (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Fong, K. C.; He, Y.; Yoon, W. H.; Choi, H. S. Angew. Chem., Int. Ed. Engl. 1999, 38, 1676-1678.
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Angew. Chem., Int. Ed. Engl.
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Nicolaou, K.C.1
Baran, P.S.2
Zhong, Y.L.3
Choi, H.S.4
Yoon, W.H.5
He, Y.6
Fong, K.C.7
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6
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0033152137
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-
Total Synthesis: (a) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Choi, H. S.; Yoon, W. H.; He, Y.; Fong, K. C. Angew. Chem., Int. Ed. Engl. 1999, 38, 1669-1675. (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Fong, K. C.; He, Y.; Yoon, W. H.; Choi, H. S. Angew. Chem., Int. Ed. Engl. 1999, 38, 1676-1678.
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Nicolaou, K.C.1
Baran, P.S.2
Zhong, Y.L.3
Fong, K.C.4
He, Y.5
Yoon, W.H.6
Choi, H.S.7
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8
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0033580868
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(b) Clive, D. L. J.; Sun, S. Y.; He, X.; Zhang, J. H.; Gagliardini, V. Tetrahedron Lett. 1999, 40, 4605-4609.
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Tetrahedron Lett.
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Clive, D.L.J.1
Sun, S.Y.2
He, X.3
Zhang, J.H.4
Gagliardini, V.5
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9
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0032556220
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(c) Chen, C.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 1998, 120, 10784-10785.
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Chen, C.1
Layton, M.E.2
Shair, M.D.3
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10
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0032479724
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(d) Kwon, O. Y.; Su, D. S.; Meng, D. F.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1877-1880.
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Kwon, O.Y.1
Su, D.S.2
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Danishefsky, S.J.6
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11
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0032479767
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(e) Kwon, O. Y.; Su, D. S.; Meng, D. F.; Deng, W.; D'Amico, D. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 1880-1882.
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Kwon, O.Y.1
Su, D.S.2
Meng, D.F.3
Deng, W.4
D'Amico, D.C.5
Danishefsky, S.J.6
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12
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0033577820
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(f) Meng, D. F.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1999, 38, 1485-1488.
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Meng, D.F.1
Danishefsky, S.J.2
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0032491844
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(g) Nicolaou, K. C.; Postema, M. H. D.; Miller, N. D.; Yang, G. Angew. Chem., Int. Ed. Engl. 1997, 36, 2821-2823.
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Nicolaou, K.C.1
Postema, M.H.D.2
Miller, N.D.3
Yang, G.4
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14
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0030749472
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(h) Nicolaou, K. C.; Harter, M. W.; Boulton, L.; Jandeleit, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1194-1196.
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Nicolaou, K.C.1
Harter, M.W.2
Boulton, L.3
Jandeleit, B.4
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15
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0033557428
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(i) Nicolaou, K. C.; Baran, P. S.; Jautelat, R.; He, Y.; Fong, K. C.; Choi, H. S.; Yoon, W. H.; Zhong, Y. L. Angew. Chem., Int. Ed. Engl. 1999, 38, 549-552.
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Nicolaou, K.C.1
Baran, P.S.2
Jautelat, R.3
He, Y.4
Fong, K.C.5
Choi, H.S.6
Yoon, W.H.7
Zhong, Y.L.8
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16
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0032514497
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(j) Waizumi, N.; Itoh, T.; Fukuyama, T. Tetrahedron Lett. 1998, 39, 6015-6018.
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Waizumi, N.1
Itoh, T.2
Fukuyama, T.3
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17
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0027503436
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Biosynthetic studies on the zaragozic acids and squalestatins: (a) Byrne, K. M.; Arison, B. H.; Nallinomstead, M.; Kaplan, L. J. Org. Chem. 1993, 58, 1019-1024. (b) Jones, C. A.; Sidebottom, P. J.; Cannell, R. J. P.; Noble, D.; Rudd, B. A. M. J. Antibiot. 1992, 45, 1492-1498.
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Byrne, K.M.1
Arison, B.H.2
Nallinomstead, M.3
Kaplan, L.4
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18
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0026701085
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Biosynthetic studies on the zaragozic acids and squalestatins: (a) Byrne, K. M.; Arison, B. H.; Nallinomstead, M.; Kaplan, L. J. Org. Chem. 1993, 58, 1019-1024. (b) Jones, C. A.; Sidebottom, P. J.; Cannell, R. J. P.; Noble, D.; Rudd, B. A. M. J. Antibiot. 1992, 45, 1492-1498.
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J. Antibiot.
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Jones, C.A.1
Sidebottom, P.J.2
Cannell, R.J.P.3
Noble, D.4
Rudd, B.A.M.5
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19
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0001720103
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(a) Baldwin, J. E.; Barton, D. H. R.; Bloomer, J. L.; Jackman, L. M.; Rodriguez-Hahn, L.; Sutheland, J. Experienta 1962, 18, 345-388.
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Experienta
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Baldwin, J.E.1
Barton, D.H.R.2
Bloomer, J.L.3
Jackman, L.M.4
Rodriguez-Hahn, L.5
Sutheland, J.6
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21
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37049040307
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(c) Barton, D. H. R.; Jackman, L. M.; Rodriguez-Hahn, L.; Sutherland, J. K. J. Chem. Soc. 1965, 1772-1778.
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J. Chem. Soc.
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Barton, D.H.R.1
Jackman, L.M.2
Rodriguez-Hahn, L.3
Sutherland, J.K.4
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25
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37049129872
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(c) Huff, R. K.; Moppett, C. E.; Sutherland, J. K. J. Chem. Soc., Perkin Trans. 1 1972, 20, 2584-2590.
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J. Chem. Soc., Perkin Trans. 1
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Huff, R.K.1
Moppett, C.E.2
Sutherland, J.K.3
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27
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0033523102
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Baldwin, J. E.; Beyeler, A.; Cox, R. J.; Keats, G.; Pritchard, G. J.; Adlington, R. M.; Watkin, D. J. Tetrahedron 1999, 55, 7363-7374.
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Tetrahedron
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Baldwin, J.E.1
Beyeler, A.2
Cox, R.J.3
Keats, G.4
Pritchard, G.J.5
Adlington, R.M.6
Watkin, D.J.7
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29
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0342389952
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In press
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Further work is required to distinguish between a covalently bound intermediate (cf. 10 to 11) and the possibility of a noncovalent Michael-type addition with concomitant decarboxylation. For a detailed discussion of the stereochemical aspects of the dimerization of 9 leading to the core structure of the CP molecules in favor of a covalently bound intermediate, see: Sulikowski, G. A.; Agnelli, F.; Corbett, R. M. J. Org. Chem. In press.
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J. Org. Chem.
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Sulikowski, G.A.1
Agnelli, F.2
Corbett, R.M.3
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30
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0342389950
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note
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The acid-catalyzed cyclodehydration of 1 to 2 has been noted. See ref 1b.
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31
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0026424346
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For a related pH-dependent secondary metabolism, see: Shah, A. J.; Tilburn, J.; Adlard, M. W.; Arst, H. N., Jr. FEMS Microbio. Lett. 1991, 77, 209-212.
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(1991)
FEMS Microbio. Lett.
, vol.77
, pp. 209-212
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Shah, A.J.1
Tilburn, J.2
Adlard, M.W.3
Arst H.N., Jr.4
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32
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0342824734
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note
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13C at other carbons.
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-
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33
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0343695196
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note
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The resonances corresponding to C(28) and C(29) variably broaden complicating comparison based on signal intensity to the natural abundance spectrum.
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35
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0342824733
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note
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13C COSY spectrum of labeled 2.
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