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(a) The Chemistry of Heterocyclic Compounds. Isoquinolines; Grethe, G., Ed.; John Wiley: New York, 1981; Part 1. The Chemistry of Heterocyclic Compounds. Isoquinolines; Kathawala, F. G., Coppola, G. M., Schuster, H. F., Eds.; John Wiley, New York, 1990; Part 2. The Chemistry of Heterocyclic Compounds. Isoquinolines; Coppola, G. M., Schuster, H. F., Eds.; John Wiley, New York, 1995; Part 3.
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Grethe, G.1
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0141441529
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John Wiley, New York
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(a) The Chemistry of Heterocyclic Compounds. Isoquinolines; Grethe, G., Ed.; John Wiley: New York, 1981; Part 1. The Chemistry of Heterocyclic Compounds. Isoquinolines; Kathawala, F. G., Coppola, G. M., Schuster, H. F., Eds.; John Wiley, New York, 1990; Part 2. The Chemistry of Heterocyclic Compounds. Isoquinolines; Coppola, G. M., Schuster, H. F., Eds.; John Wiley, New York, 1995; Part 3.
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The Chemistry of Heterocyclic Compounds. Isoquinolines
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Kathawala, F.G.1
Coppola, G.M.2
Schuster, H.F.3
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3
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0141553060
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John Wiley, New York
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(a) The Chemistry of Heterocyclic Compounds. Isoquinolines; Grethe, G., Ed.; John Wiley: New York, 1981; Part 1. The Chemistry of Heterocyclic Compounds. Isoquinolines; Kathawala, F. G., Coppola, G. M., Schuster, H. F., Eds.; John Wiley, New York, 1990; Part 2. The Chemistry of Heterocyclic Compounds. Isoquinolines; Coppola, G. M., Schuster, H. F., Eds.; John Wiley, New York, 1995; Part 3.
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(b) For a recent review of these alkaloids, see: Ozturk, T. The Alkaloids. Cordell, G. A., Ed.; Academic Press, San Diego, 2000; Vol. 53, p 120.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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For a comprehensive account of the chemistry and biology of these compounds, see: (a) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. (b) Myers, A. G.; Kung, D. W. J. Am. Chem. Soc. 1999, 121, 10828. (c) Myers, A. G.; Kung, D. W.; Zhong, B.; Movassaghi, M.; Kwon, S. J. Am. Chem. Soc. 1999, 121, 8401. (d) Kubo, A.; Saito, N.; Yamato, H.; Masubuchi, K.; Nakamura, M. J. Org. Chem. 1988, 53, 4295. (e) Saito, N.; Harada, S.; Yamashita, M.; Saito, T.; Yamaguchi, K.; Kubo, A. Tetrahedron 1995, 51, 8213. (f) Fukuyama, T.; Sachleben, R. A. J. Am. Chem. Soc. 1982, 104, 4957. (g) Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. (h) Zhou, B.; Edmondson, S.; Padron, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2039. (i) Zhou, B.; Guo, J.; Danishefsky, S. J. Tetrahedron Lett. 2000, 41, 2043. (j) Zhou, B.; Guo, J.; Danishefsky, S. J. Org. Lett. 2002, 4, 43.
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Roesch, K. R.; Larock, R. C. J. Org. Chem. 2002, 67, 86. In this paper, the yield of 3-hydroxymethylisoquinoline was 0% when propargyl alcohol was used (Table 3, entry 5 in the above reference). Simply using protected derivatives as in Scheme 3 works well.
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24
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0141553058
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note
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Enantiomers were separated using chiral HPLC.
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26
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0001183472
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Closest analogy to the type of reaction is the intramolecular Schmidt rearrangement. (a) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449. (b) Mossman, C. J.; Aubé, J. Tetrahedron 1996, 52, 3403.
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0030028492
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Closest analogy to the type of reaction is the intramolecular Schmidt rearrangement. (a) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449. (b) Mossman, C. J.; Aubé, J. Tetrahedron 1996, 52, 3403.
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