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1
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85030199761
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Howard Hughes Medical Institute Predoctoral Fellow
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1. Howard Hughes Medical Institute Predoctoral Fellow
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2
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0027518332
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2. (a) Bergstrom, J. D.; Kurtz, M. M.; Rew, D. J.; Amend, A. M.; Karkas, J. D.; Bostedor, R. G.; Bansal, V. S.; Dufresne, C.; VanMiddlesworth, R. L.; Hensens, O. D.; Liesch, J. M.; Zink, D. L.; Wilson, K. E.; Onishi, J.; Milligan, J. A.; Bills, G.; Kaplan, L.; Omstead, M. N.; Jenkins, R. G.; Huang, L.; Meinz, M. S.; Quinn, L.; Burg, R. W.; Kong, Y. L.; Mochales, S.; Mojena, M.; Martin, I.; Pelaez, F.; Diez, M. T.; Alberts, A. W. Proc. Natl. Acad. Sci. USA 1993, 90, 80.
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(1993)
Proc. Natl. Acad. Sci. USA
, vol.90
, pp. 80
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Bergstrom, J.D.1
Kurtz, M.M.2
Rew, D.J.3
Amend, A.M.4
Karkas, J.D.5
Bostedor, R.G.6
Bansal, V.S.7
Dufresne, C.8
VanMiddlesworth, R.L.9
Hensens, O.D.10
Liesch, J.M.11
Zink, D.L.12
Wilson, K.E.13
Onishi, J.14
Milligan, J.A.15
Bills, G.16
Kaplan, L.17
Omstead, M.N.18
Jenkins, R.G.19
Huang, L.20
Meinz, M.S.21
Quinn, L.22
Burg, R.W.23
Kong, Y.L.24
Mochales, S.25
Mojena, M.26
Martin, I.27
Pelaez, F.28
Diez, M.T.29
Alberts, A.W.30
more..
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3
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0026635536
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(b) Baxter, A.; Fitzgerald, B. J.; Hutson, J. L.; McCarthy, A. D.; Motteram, J. M.; Ross, B. C.; Sapra, M.; Snowden, M. A.; Watson, N. S.; Williams, R. J.; Wright, C. J. Biol. Chem. 1992, 267, 11705.
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(1992)
J. Biol. Chem.
, vol.267
, pp. 11705
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Baxter, A.1
Fitzgerald, B.J.2
Hutson, J.L.3
McCarthy, A.D.4
Motteram, J.M.5
Ross, B.C.6
Sapra, M.7
Snowden, M.A.8
Watson, N.S.9
Williams, R.J.10
Wright, C.11
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6
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84989565540
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(b) Nicolaou, K. C.; Yue, E. W.; La Greca, S.; Nadin, A.; Yang, Z.; Leresche, J. E.; Tsuri, T.; Naniwa, Y.; De Riccardis, F. Chem. Eur. J. 1995, 1, 467.
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(1995)
Chem. Eur. J.
, vol.1
, pp. 467
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Nicolaou, K.C.1
Yue, E.W.2
La Greca, S.3
Nadin, A.4
Yang, Z.5
Leresche, J.E.6
Tsuri, T.7
Naniwa, Y.8
De Riccardis, F.9
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7
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0028608155
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(c) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111.
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(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 12111
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Evans, D.A.1
Barrow, J.C.2
Leighton, J.L.3
Robichaud, A.J.4
Sefkow, M.5
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8
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0027764402
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5. Other synthetic studies of zaragozic acid: (a) Abdel-Rahman, H.; Adams, J. P.; Boyles, A. L.; Kelly, M. J.; Mansfield, D. J.; Procopiou, P. A.; Roberts, S. M.; Slee, D. H.; Watson, N. S. J. Chem. Soc., Chem. Commun. 1993, 1839.
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(1993)
J. Chem. Soc., Chem. Commun.
, pp. 1839
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Abdel-Rahman, H.1
Adams, J.P.2
Boyles, A.L.3
Kelly, M.J.4
Mansfield, D.J.5
Procopiou, P.A.6
Roberts, S.M.7
Slee, D.H.8
Watson, N.S.9
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9
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0027733687
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(b) Abdel-Rahman, H.; Adams, J. P.; Boyles, A. L.; Kelly, M. J.; Mansfield, D. J.; Procopiou, P. A.; Roberts, S. M.; Slee, D. H.; Sidebottom, P. J.; Sik, V.; Watson, N. S. J. Chem. Soc., Chem. Commun. 1993, 1841.
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(1993)
J. Chem. Soc., Chem. Commun.
, pp. 1841
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Abdel-Rahman, H.1
Adams, J.P.2
Boyles, A.L.3
Kelly, M.J.4
Mansfield, D.J.5
Procopiou, P.A.6
Roberts, S.M.7
Slee, D.H.8
Sidebottom, P.J.9
Sik, V.10
Watson, N.S.11
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10
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37049074168
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(c) Abdel-Rahman, H.; Adams, J. P.; Boyles, A. L. J. Chem. Soc., Perkin Trans. 1 1994, 1259.
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(1994)
J. Chem. Soc., Perkin Trans. 1
, pp. 1259
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Abdel-Rahman, H.1
Adams, J.P.2
Boyles, A.L.3
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12
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0028107116
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(e) Aggarwal, V. K.; Wang, M. F.; Zaparucha, A. J. Chem. Soc., Chem. Commun. 1994, 87.
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(1994)
J. Chem. Soc., Chem. Commun.
, pp. 87
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Aggarwal, V.K.1
Wang, M.F.2
Zaparucha, A.3
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15
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0029015581
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(h) Caron, S.; McDonald, A. I.; Heathcock, C. H. J. Org. Chem. 1995, 60, 2780.
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(1995)
J. Org. Chem.
, vol.60
, pp. 2780
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Caron, S.1
McDonald, A.I.2
Heathcock, C.H.3
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16
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0019499120
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6. For other examples of the use of Norrish reactions to generate oxygen substituted biradicals, see: (a) Kozluk, T.; Cottier, L.; Descotes, G. Tetrahedron 1981, 37, 1875.
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(1981)
Tetrahedron
, vol.37
, pp. 1875
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Kozluk, T.1
Cottier, L.2
Descotes, G.3
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17
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0019128580
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(b) Remy, G.; Cottier, L.; Descotes, G. Can. J. Chem. 1980, 58, 2660.
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(1980)
Can. J. Chem.
, vol.58
, pp. 2660
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Remy, G.1
Cottier, L.2
Descotes, G.3
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18
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84914264396
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(c) Remy, G.; Cottier, L.; Descotes, G. J. Carbohydr. Chem. 1983, 1, 37.
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(1983)
J. Carbohydr. Chem.
, vol.1
, pp. 37
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Remy, G.1
Cottier, L.2
Descotes, G.3
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23
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33947090503
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(c) Wagner, P. J.; Kelso, P. A.; Kemppainen, A. E.; McGrath, J. M.; Schott, H. N.; Zepp, R. G. J. Am. Chem. Soc. 1972, 94, 7506.
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(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 7506
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Wagner, P.J.1
Kelso, P.A.2
Kemppainen, A.E.3
McGrath, J.M.4
Schott, H.N.5
Zepp, R.G.6
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24
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33947088997
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(d) Wagner, P. J.; Kelso, P. A.; Zepp, R. G. J. Am. Chem. Soc. 1972, 94, 7480.
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(1972)
J. Am. Chem. Soc.
, vol.94
, pp. 7480
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Wagner, P.J.1
Kelso, P.A.2
Zepp, R.G.3
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26
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85030208051
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note
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9. (a) An inseparable 2:1 mixture of compound 7 and its diastereomer at the acetal carbon was produced. (b) The aldehyde that was derived from the minor diastereomer from the previous step was also isolated in 14% yield after the subsequent ozonolysis step.
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27
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85030198080
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note
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10. The stereochemistry at the newly-formed carbinol carbon of 9 was definitively determined by NOE difference NMR spectroscopy. The presence of a crosspeak correlating the proton of the carbinol center with the ketal carbon in the HMBC spectrum further secured the structure of 9.
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28
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85030203138
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note
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11. Other products that appear to arise from abstraction of hydrogen atoms from either the ether methylene or from the ring fusion methine were also produced in minor (<10%) amounts.
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