-
1
-
-
0037458793
-
-
For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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(2003)
J. Org. Chem.
, vol.68
, pp. 1489
-
-
Bunch, L.1
Liljefors, T.2
Greenwood, J.R.3
Frydenvang, K.4
Brauner-Osborne, H.5
Krogsgaard-Larsen, P.6
Madsen, U.7
-
2
-
-
0033582986
-
-
For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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(1999)
J. Org. Chem.
, vol.64
, pp. 2050
-
-
Hart, B.P.1
Rapoport, H.2
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3
-
-
0032813742
-
-
For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
-
(1999)
Synlett
, pp. 1091
-
-
Piotroski, D.W.1
-
4
-
-
0005761614
-
-
For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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(1988)
Bioorg. Med. Chem. Lett.
, vol.8
, pp. 3101
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-
Esslinger, C.S.1
Koch, H.P.2
Kavanaugh, M.P.3
Philips, D.P.4
Chamberlin, A.R.5
Thompson, C.M.6
Bridges, R.J.7
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5
-
-
0032732281
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For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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(1999)
Mol. Pharmacol.
, vol.56
, pp. 1095
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-
Koch, H.P.1
Kavanaugh, M.P.2
Esslinger, C.S.3
Zerangue, N.4
Humphrey, J.M.5
Amara, S.G.6
Chamberlain, A.R.7
Bridges, R.J.8
-
6
-
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0025190239
-
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For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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(1990)
Biopolymers
, vol.29
, pp. 407
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Mapelli, C.1
Van Halbeek, H.2
Stammer, C.H.3
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7
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33847086169
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For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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(1980)
J. Am. Chem. Soc.
, vol.102
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Bell, E.A.1
Qureshi, M.Y.2
Pryce, R.J.3
Janzen, D.H.4
Lemke, P.5
Clardy, J.6
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8
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0033576444
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For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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(1999)
Org. Lett.
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Han, W.1
Pelletier, J.C.2
Mersinger, L.3
Ketner, C.A.4
Hodge, C.N.5
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9
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0005761614
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For leading references with bridged pyrrolidines, see: (a) Bunch, L.; Liljefors, T.; Greenwood, J. R.; Frydenvang, K.; Brauner-Osborne, H.; Krogsgaard-Larsen, P.; Madsen U. J. Org. Chem. 2003, 68, 1489. (b) Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050. (c) Piotroski, D. W. Synlett 1999, 1091. (d) Esslinger, C. S.; Koch, H. P.; Kavanaugh, M. P.; Philips, D. P.; Chamberlin, A. R.; Thompson, C. M.; Bridges, R. J. Bioorg. Med. Chem. Lett. 1988, 8, 3101. (e) Koch, H. P.; Kavanaugh, M. P.; Esslinger, C. S.; Zerangue, N.; Humphrey, J. M.; Amara, S. G.; Chamberlain, A. R.; Bridges, R. J. Mol. Pharmacol. 1999, 56, 1095. (f) Mapelli, C.; van Halbeek, H.; Stammer, C. H. Biopolymers 1990, 29, 407. (g) Bell, E. A.; Qureshi, M. Y.; Pryce, R. J.; Janzen, D. H.; Lemke, P.; Clardy, J. J. Am. Chem. Soc. 1980, 102, 1409. (h) Han, W.; Pelletier, J. C.; Mersinger, L.; Ketner, C. A.; Hodge, C. N. Org. Lett. 1999, 1, 1875. (i) Park, T. H.; Ha, Y. H.; Jeong, D. Y. Patent Application WO 98-KR246 19989898; Chem. Abstr. 1999, 130, 182388.
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Park, T.H.1
Ha, Y.H.2
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For a review of 4-hydroxy-L-proline as a building block, see: Remuzon, P. Tetrahedron 1996, 52, 13803.
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For generation of nonproteinogenic amino acids from 4-hydroxyproline, see: (a) Cheng, W.-C.; Liu, Y.; Wong, M.; Olmstead, M. M.; Lam, K. S.; Kurth, M. J. J. Org. Chem. 2002, 67, 5673. (b) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038.
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Liu, Y.2
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Lam, K.S.5
Kurth, M.J.6
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13
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0025831274
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For generation of nonproteinogenic amino acids from 4-hydroxyproline, see: (a) Cheng, W.-C.; Liu, Y.; Wong, M.; Olmstead, M. M.; Lam, K. S.; Kurth, M. J. J. Org. Chem. 2002, 67, 5673. (b) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038.
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For generation of nonproteinogenic amino acids from 4-hydroxyproline, see: (a) Cheng, W.-C.; Liu, Y.; Wong, M.; Olmstead, M. M.; Lam, K. S.; Kurth, M. J. J. Org. Chem. 2002, 67, 5673. (b) Webb, T. R.; Eigenbrot, C. J. Org. Chem. 1991, 56, 3009. (c) Tamaki, M.; Han, G.; Hruby, V. J. J. Org. Chem. 2001, 66, 1038.
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Han, G.2
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For aminonucleotides based on 4-hydroxyprolinol, see: (a) Reed, M. W.; Lukhtanov, E. A.; Gorn, V. V.; Lucas, D. D.; Zhou, J. H.; Pai, S. B.; Cheng, Y.; Meyer, R. B., Jr. J. Med. Chem. 1995, 38, 4587. (b) Peterson, M. L.; Vince, R. J. Med. Chem. 1991, 34, 2787.
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Zhou, J.H.5
Pai, S.B.6
Cheng, Y.7
Meyer Jr., R.B.8
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0026079802
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For aminonucleotides based on 4-hydroxyprolinol, see: (a) Reed, M. W.; Lukhtanov, E. A.; Gorn, V. V.; Lucas, D. D.; Zhou, J. H.; Pai, S. B.; Cheng, Y.; Meyer, R. B., Jr. J. Med. Chem. 1995, 38, 4587. (b) Peterson, M. L.; Vince, R. J. Med. Chem. 1991, 34, 2787.
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For peptide nucleic acids from 4-hydroxyproline, see: (a) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 547. (b) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 555. (c) Westwood, N. B.; Walker, R. T. Tetrahedron 1998, 54, 13391. (d) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 539. (e) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Schwenner, E.; Stropp, U.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 681. (f) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Stropp, U.; Schwenner, E.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 687. (g) Puschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161.
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Lowe, G.1
Vilaivan, T.2
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For peptide nucleic acids from 4-hydroxyproline, see: (a) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 547. (b) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 555. (c) Westwood, N. B.; Walker, R. T. Tetrahedron 1998, 54, 13391. (d) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 539. (e) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Schwenner, E.; Stropp, U.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 681. (f) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Stropp, U.; Schwenner, E.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 687. (g) Puschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161.
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Vilaivan, T.2
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0032578672
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For peptide nucleic acids from 4-hydroxyproline, see: (a) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 547. (b) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 555. (c) Westwood, N. B.; Walker, R. T. Tetrahedron 1998, 54, 13391. (d) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 539. (e) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Schwenner, E.; Stropp, U.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 681. (f) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Stropp, U.; Schwenner, E.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 687. (g) Puschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161.
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For peptide nucleic acids from 4-hydroxyproline, see: (a) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 547. (b) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 555. (c) Westwood, N. B.; Walker, R. T. Tetrahedron 1998, 54, 13391. (d) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 539. (e) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Schwenner, E.; Stropp, U.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 681. (f) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Stropp, U.; Schwenner, E.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 687. (g) Puschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161.
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For peptide nucleic acids from 4-hydroxyproline, see: (a) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 547. (b) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 555. (c) Westwood, N. B.; Walker, R. T. Tetrahedron 1998, 54, 13391. (d) Lowe, G.; Vilaivan, T. J. Chem. Soc., Perkin Trans. 1 1997, 539. (e) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Schwenner, E.; Stropp, U.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 681. (f) Jordan, S.; Schwemler, C.; Kosch, W.; Kretschmer, A.; Stropp, U.; Schwenner, E.; Mielke, B. Bioorg. Med. Chem. Lett. 1997, 7, 687. (g) Puschl, A.; Tedeschi, T.; Nielsen, P. E. Org. Lett. 2000, 2, 4161.
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The rearrangement of alcohol 22 might be envisioned as occurring through a series of steps shown in Scheme 5. An alcohol proton catalyzed ring opening could give a β-silyl cation i. A subsequent 1,2-alkyl shift gives a ring-enlarged cation ii. Proton loss generates an allylic silane iii. Desilylation accompanied by bromide elimination gives diene iv and a series of acid-catalyzed proton transfers affords ketone 23.
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