Synthesis of new potential aminopeptidase inhibitors by Lewis acid induced rearrangement of 2,3 epoxy amines and regiospecific nucleophilic trapping of aziridinium ion intermediates with α-amino esters

Tetrahedron

Volumn 53, Issue 46, 1997, Pages 15729-15742

  Liu, Quanying ^a   Marchington, Allan P ^b,c   Rayner, Christopher M ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c Sheraton House   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOPEPTIDASE; AZIRIDINE; ENZYME INHIBITOR;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0030734433     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00849-1     Document Type: Article

References (70)

1. Rich, D.H. Comprehensive Medicinal Chemistry, Eds.; Hansch, C.; Sammes, P. G.; Taylor, J.B. Pergamon, New York, 1990, 391; Gante, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720; for other examples of biologically active amino alcohols see: Reetz, M.T. Angew. Chem., Int. Ed. Engl., 1991, 30, 1531-1546; Ohfune, Y. Acc. Chem. Res., 1992, 25, 360-366; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051-1078; Golebiowski, A.; Jurczak, J. Synlett, 1993, 241-245; Kunieda, T.; Ishizuka, T. Studies in Natural Products Chemistry, Ed: Atta-ur-Rahman, Elsevier, New York. 1993, 12, 411.
2. Rich, D.H. Comprehensive Medicinal Chemistry, Eds.; Hansch, C.; Sammes, P. G.; Taylor, J.B. Pergamon, New York, 1990, 391; Gante, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720; for other examples of biologically active amino alcohols see: Reetz, M.T. Angew. Chem., Int. Ed. Engl., 1991, 30, 1531-1546; Ohfune, Y. Acc. Chem. Res., 1992, 25, 360-366; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051-1078; Golebiowski, A.; Jurczak, J. Synlett, 1993, 241-245; Kunieda, T.; Ishizuka, T. Studies in Natural Products Chemistry, Ed: Atta-ur-Rahman, Elsevier, New York. 1993, 12, 411.
3. Rich, D.H. Comprehensive Medicinal Chemistry, Eds.; Hansch, C.; Sammes, P. G.; Taylor, J.B. Pergamon, New York, 1990, 391; Gante, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720; for other examples of biologically active amino alcohols see: Reetz, M.T. Angew. Chem., Int. Ed. Engl., 1991, 30, 1531-1546; Ohfune, Y. Acc. Chem. Res., 1992, 25, 360-366; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051-1078; Golebiowski, A.; Jurczak, J. Synlett, 1993, 241-245; Kunieda, T.; Ishizuka, T. Studies in Natural Products Chemistry, Ed: Atta-ur-Rahman, Elsevier, New York. 1993, 12, 411.
4. Rich, D.H. Comprehensive Medicinal Chemistry, Eds.; Hansch, C.; Sammes, P. G.; Taylor, J.B. Pergamon, New York, 1990, 391; Gante, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720; for other examples of biologically active amino alcohols see: Reetz, M.T. Angew. Chem., Int. Ed. Engl., 1991, 30, 1531-1546; Ohfune, Y. Acc. Chem. Res., 1992, 25, 360-366; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051-1078; Golebiowski, A.; Jurczak, J. Synlett, 1993, 241-245; Kunieda, T.; Ishizuka, T. Studies in Natural Products Chemistry, Ed: Atta-ur-Rahman, Elsevier, New York. 1993, 12, 411.
5. Rich, D.H. Comprehensive Medicinal Chemistry, Eds.; Hansch, C.; Sammes, P. G.; Taylor, J.B. Pergamon, New York, 1990, 391; Gante, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720; for other examples of biologically active amino alcohols see: Reetz, M.T. Angew. Chem., Int. Ed. Engl., 1991, 30, 1531-1546; Ohfune, Y. Acc. Chem. Res., 1992, 25, 360-366; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051-1078; Golebiowski, A.; Jurczak, J. Synlett, 1993, 241-245; Kunieda, T.; Ishizuka, T. Studies in Natural Products Chemistry, Ed: Atta-ur-Rahman, Elsevier, New York. 1993, 12, 411.
6. Rich, D.H. Comprehensive Medicinal Chemistry, Eds.; Hansch, C.; Sammes, P. G.; Taylor, J.B. Pergamon, New York, 1990, 391; Gante, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720; for other examples of biologically active amino alcohols see: Reetz, M.T. Angew. Chem., Int. Ed. Engl., 1991, 30, 1531-1546; Ohfune, Y. Acc. Chem. Res., 1992, 25, 360-366; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051-1078; Golebiowski, A.; Jurczak, J. Synlett, 1993, 241-245; Kunieda, T.; Ishizuka, T. Studies in Natural Products Chemistry, Ed: Atta-ur-Rahman, Elsevier, New York. 1993, 12, 411.
7. Rich, D.H. Comprehensive Medicinal Chemistry, Eds.; Hansch, C.; Sammes, P. G.; Taylor, J.B. Pergamon, New York, 1990, 391; Gante, J. Angew. Chem., Int. Ed. Engl., 1994, 33, 1699-1720; for other examples of biologically active amino alcohols see: Reetz, M.T. Angew. Chem., Int. Ed. Engl., 1991, 30, 1531-1546; Ohfune, Y. Acc. Chem. Res., 1992, 25, 360-366; Yokomatsu, T.; Yuasa, Y.; Shibuya, S. Heterocycles, 1992, 33, 1051-1078; Golebiowski, A.; Jurczak, J. Synlett, 1993, 241-245; Kunieda, T.; Ishizuka, T. Studies in Natural Products Chemistry, Ed: Atta-ur-Rahman, Elsevier, New York. 1993, 12, 411.
8. Heerding, J.M.; Lampe, J.W.; Darges, J. W.; Stamper, M.L. Bioorg. Med. Chem. Lett., 1995, 5, 1839-1842; Tanner, D.; Almario, A.; Hogberg, T. Tetrahedron, 1995, 51, 6061-6070; See also: Konig, W. A.; Sinnwell, V; Witt, S.; Kneifel, H. Chem. Ber., 1980, 113, 2221-2226.
9. Heerding, J.M.; Lampe, J.W.; Darges, J. W.; Stamper, M.L. Bioorg. Med. Chem. Lett., 1995, 5, 1839-1842; Tanner, D.; Almario, A.; Hogberg, T. Tetrahedron, 1995, 51, 6061-6070; See also: Konig, W. A.; Sinnwell, V; Witt, S.; Kneifel, H. Chem. Ber., 1980, 113, 2221-2226.
10. Heerding, J.M.; Lampe, J.W.; Darges, J. W.; Stamper, M.L. Bioorg. Med. Chem. Lett., 1995, 5, 1839-1842; Tanner, D.; Almario, A.; Hogberg, T. Tetrahedron, 1995, 51, 6061-6070; See also: Konig, W. A.; Sinnwell, V; Witt, S.; Kneifel, H. Chem. Ber., 1980, 113, 2221-2226.
11. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
12. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
13. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
14. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
15. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
16. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
17. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
18. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
19. Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H., J. Med. Chem., 1977, 20, 510-515; Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211; Ocain, T.D.; Rich, D.H. J. Med. Chem., 1988, 31, 2193-2199. For synthetic approaches to Bestatin see: Palomo, C.; Arrieta, A.; Cossio, F.P.; Aizpurua, J.M.; Mielgo, A.; Aurrekoetxea, N., Tetrahedron Lett., 1990, 31, 6429-6432. See also: Kempf, D. J.; Norbeck, D.W.; Codacovi, L.M.; Wang, X. C.; Kohlbrenner, W. E.; Wideburg, N. E.; Paul, D. A.; Knigge, M.F.; Vasavanonda, S.; Craig-Kennard, A.; Saldivar, A.; Rosenbrook Jr., W.; Plattner, J.J.; Erickson, J. J. Med. Chem., 1990, 33, 2687-2689; Kahn, M.; Nakanishi, H.; Chrusciel, R.A.; Fitzpatrick, D.; Johnson, M.E. J. Med. Chem., 1991, 34, 3395-3399; Kobayashi, Y.; Nakatani, K.; Ito, Y.; Terashima, S. Chemistry Lett., 1990, 1709-1710; Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Umeyama, H.; Ishida, T.; Kiso, Y., J. Med. Chem., 1990, 33, 2707-2714; Thaisrivongs, S.; Pals, D.T.; DuCharme, D.W.; Turner, S.R.; DeGraaf, G.L.; Lawson, J.A.; Couch, S.J.; Williams, M.V., J. Med. Chem., 1991, 34, 633-642.
20. Rayner, C.M. Synlett, 1997, 11-21; see also: Westwell, A.D.; Thornton-Pett, M.; Rayner, C.M. J. Chem. Soc., Perkin Trans. 1, 1995, 847-959.
21. Rayner, C.M. Synlett, 1997, 11-21; see also: Westwell, A.D.; Thornton-Pett, M.; Rayner, C.M. J. Chem. Soc., Perkin Trans. I, 1995, 847-959.
22. a) Gill, D.M.; Pegg, N.A.; Rayner, C.M. Tetrahedron, 1997, 53, 3383-3394;
23. b) idem, ibid., 1996, 52, 3609-3630;
24. c) idem, Synlett, 1995, 1275-1276;
25. d) idem, Tetrahedron Lett., 1995, 36, 8327-8330;
26. e) J. Chem. Soc., Perkin Trans. I, 1993, 1371-1372.
27. a) Liu, Q.; Marchington, A.P.; Boden, N.; Rayner, C.M. J. Chem. Soc., Perkin Trans. 1, 1997, 511-525;
28. b) idem, Synlett, 1995, 1037-1039;
29. c) Liu, Q.; Simms, M.J.; Boden, N.; Rayner, C.M. J. Chem. Soc., Perkin Trans. 1, 1994, 1363-1365;
30. d) for recent studies involving aziridinium ions see: Richardson, P.F.; Nelson, L.T.J.; Sharpless, K.B. Tetrahedron Lett., 1995, 36, 9241-9244; O'Brien, P.; Poumellec, P. ibid., 1996, 37, 5619-5622; de Sousa, S.E.; O'Brien, P. ibid., 1997, 38, 4885-4888;
31. d) for recent studies involving aziridinium ions see: Richardson, P.F.; Nelson, L.T.J.; Sharpless, K.B. Tetrahedron Lett., 1995, 36, 9241-9244; O'Brien, P.; Poumellec, P. ibid., 1996, 37, 5619-5622; de Sousa, S.E.; O'Brien, P. ibid., 1997, 38, 4885-4888;
32. d) for recent studies involving aziridinium ions see: Richardson, P.F.; Nelson, L.T.J.; Sharpless, K.B. Tetrahedron Lett., 1995, 36, 9241-9244; O'Brien, P.; Poumellec, P. ibid., 1996, 37, 5619-5622; de Sousa, S.E.; O'Brien, P. ibid., 1997, 38, 4885-4888;
33. e) for other related rearrangements see: Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Otaka, A.; Tamamura, H.; Fujii, N.; Mimura, N.; Miwa, Y.; Taga, T.; Chounan, Y.; Yamamoto, Y. J. Org. Chem., 1995, 60, 2044-2058; Nakai, K.; Ibuka, T.; Otaka, A.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett., 1995, 36, 6247-6250 and references cited therein;
34. e) for other related rearrangements see: Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Otaka, A.; Tamamura, H.; Fujii, N.; Mimura, N.; Miwa, Y.; Taga, T.; Chounan, Y.; Yamamoto, Y. J. Org. Chem., 1995, 60, 2044-2058; Nakai, K.; Ibuka, T.; Otaka, A.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett., 1995, 36, 6247-6250 and references cited therein;
35. Dunlap, B.E.; Dunlap, S.A.; Rich, D.H. Scand. J. Immunol., 1984, 20, 237-245; Schorlemmer, H.; Basslet, K.; Sedlacek, H. Cancer Res., 1983, 43, 4148-4153.
36. Dunlap, B.E.; Dunlap, S.A.; Rich, D.H. Scand. J. Immunol., 1984, 20, 237-245; Schorlemmer, H.; Basslet, K.; Sedlacek, H. Cancer Res., 1983, 43, 4148-4153.
37. Barclay, R.K.; Phillipps, M.A. Biochem. Biophys. Res. Commun., 1980, 96, 1732-1738; Roques, B.P.; Fournie-Zaluski, M.C.; Soroca, E.; Lecomte, J.M.; Malfroy, B.; Lloreus, C.; Schwartz, J.-C. Nature (London), 1980, 288, 286-288.
38. Barclay, R.K.; Phillipps, M.A. Biochem. Biophys. Res. Commun., 1980, 96, 1732-1738; Roques, B.P.; Fournie-Zaluski, M.C.; Soroca, E.; Lecomte, J.M.; Malfroy, B.; Lloreus, C.; Schwartz, J.-C. Nature (London), 1980, 288, 286-288.
39. Norman, B.H.; Morris, M.L. Tetrahedron Lett., 1992, 33, 6803-6806 and refs. cited therein.
40. Gordon, E.M.; Godfrey, J.D.; Delaney, N.G.; Asaad, M.M.; Von Langen, D.; Cushman, D.W. J. Med. Chem., 1988, 31, 2199-2211.
41. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
42. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
43. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
44. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
45. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
46. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
47. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
48. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
49. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
50. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
51. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
52. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
53. For other examples see: Badorrey, R.; Cativiela, C.; DiazDeVillegas, M.D.; Galvez, J.A.; Lapena, Y. Tetrahedron Asymm., 1997, 8, 311-317; Abbenante, G.; Bergman, D.A.; Brinkworth, R.I.; March, D.R.; Reid, R.C.; Hunt, P.A.; James, I.W.; Dancer, R.J.; Garnham, B.; Stoermer, M.L.; Fairlie, D.P. Bioorg. Med. Chem. Lett., 1996, 6, 2531-2536; Kranz, M.; Kessler, H. Tetrahedron Lett., 1996, 37, 5359-5362; Moree, W.J.; Vandermarel, G.A.; Liskamp, R.J. J. Org. Chem., 1995, 60, 5157-5169; Rotella, D.P. Tetrahedron Lett., 1995, 36, 5453-5456; Williams, R.M.; Colson, P.J.; Zhai, W.X. Tetrahedron Lett., 1994, 35, 9371-9374; Wipf, P.; Fritch, P.C. J. Org. Chem., 1994, 59, 4875-4886; Askin, D.; Wallace, M.A.; Vacca, J.P.; Reamer, R.A.; Volante, R.P.; Shinkai, I. J. Org. Chem., 1992, 57, 2771-2773; Fincham, C.I.; Higginbottom, M.; Hill, D.R.; Horwell, D.C.; O'Toole, J.C.; Ratcliffe, G.S.; Rees, D.C.; Roberts, E. J. Med. Chem., 1992, 35, 1472-1484; Hoffman, R.V.; Kim, H.-O. Tetrahedron Lett., 1992, 33, 3579-3582; Thompson, W.J.; Ball, R.G.; Darke, P.L.; Zugay, J.A.; Thies, J.E. Tetrahedron Lett., 1992, 33, 2957-2960; Baker, W.R.; Condon, S.L. Tetrahedron Lett., 1992, 33, 1581-1584; Poss, M.A.; Reid, J.A. Tetrahedron Lett., 1992, 33, 1411-1415.
54. Sharpless, K.B.; Exon, C.M.; Regenye, R. Org. Synth., 1984, 63, 66-78; Katsuki, T.; Sharpless, K.B. J. Amer. Chem. Soc., 1980, 102, 5974-5976; Hill, J.G.; Finn, M.G.; Sharpless, K.B. Asymmetric Synthesis, Ed. Morrison, J.D., Academic Press, New York, 1985, 5.
55. Sharpless, K.B.; Exon, C.M.; Regenye, R. Org. Synth., 1984, 63, 66-78; Katsuki, T.; Sharpless, K.B. J. Amer. Chem. Soc., 1980, 102, 5974-5976; Hill, J.G.; Finn, M.G.; Sharpless, K.B. Asymmetric Synthesis, Ed. Morrison, J.D., Academic Press, New York, 1985, 5.
56. Sharpless, K.B.; Exon, C.M.; Regenye, R. Org. Synth., 1984, 63, 66-78; Katsuki, T.; Sharpless, K.B. J. Amer. Chem. Soc., 1980, 102, 5974-5976; Hill, J.G.; Finn, M.G.; Sharpless, K.B. Asymmetric Synthesis, Ed. Morrison, J.D., Academic Press, New York, 1985, 5.
57. Laguzza, B.C.; Ganem, B. Tetrahedron Lett., 1981, 22, 1483-1486; Moreau, B.; Lavielle, S.; Marquet, A. Tetrahedron Lett., 1977, 18, 2591-2594; Sundberg, R.J.; Hamilton, G.S.; Laurino, P.J. J. Org. Chem., 1988, 53, 976-983.
58. Laguzza, B.C.; Ganem, B. Tetrahedron Lett., 1981, 22, 1483-1486; Moreau, B.; Lavielle, S.; Marquet, A. Tetrahedron Lett., 1977, 18, 2591-2594; Sundberg, R.J.; Hamilton, G.S.; Laurino, P.J. J. Org. Chem., 1988, 53, 976-983.
59. Laguzza, B.C.; Ganem, B. Tetrahedron Lett., 1981, 22, 1483-1486; Moreau, B.; Lavielle, S.; Marquet, A. Tetrahedron Lett., 1977, 18, 2591-2594; Sundberg, R.J.; Hamilton, G.S.; Laurino, P.J. J. Org. Chem., 1988, 53, 976-983.
60. Hartung, W.H.; Simonoff, R. Org. React., 1953, 7, 275-278; Jacobi, P.A.; Martinelli, M.J.; Polanc, S. J. Amer. Chem. Soc., 1984, 106, 5594-5598; Overman, L.E.; Mendelson, L.T.; Jacobsen, E.J. J. Amer. Chem. Soc., 1983, 105, 6629-6637.
61. Hartung, W.H.; Simonoff, R. Org. React., 1953, 7, 275-278; Jacobi, P.A.; Martinelli, M.J.; Polanc, S. J. Amer. Chem. Soc., 1984, 106, 5594-5598; Overman, L.E.; Mendelson, L.T.; Jacobsen, E.J. J. Amer. Chem. Soc., 1983, 105, 6629-6637.
62. Hartung, W.H.; Simonoff, R. Org. React., 1953, 7, 275-278; Jacobi, P.A.; Martinelli, M.J.; Polanc, S. J. Amer. Chem. Soc., 1984, 106, 5594-5598; Overman, L.E.; Mendelson, L.T.; Jacobsen, E.J. J. Amer. Chem. Soc., 1983, 105, 6629-6637.
63. Moulines, J.; Charpentier, P.; Bats, J.-P.; Nuhrich, A.; Lamidey, A.-M. Tetrahedron Lett., 1992, 33, 487-490; see also: Najime, R.; Pilard, S.; Vaultier, M. Tetrahedron Lett., 1992, 33, 5351-5354; Kowollik, W.; Janairo, G.; Voelter, W. Justus Liebigs Ann. Chem., 1988, 427-431; Tanner, D.; Somfai. P. Tetrahedron, 1988, 44, 619-624.
64. Moulines, J.; Charpentier, P.; Bats, J.-P.; Nuhrich, A.; Lamidey, A.-M. Tetrahedron Lett., 1992, 33, 487-490; see also: Najime, R.; Pilard, S.; Vaultier, M. Tetrahedron Lett., 1992, 33, 5351-5354; Kowollik, W.; Janairo, G.; Voelter, W. Justus Liebigs Ann. Chem., 1988, 427-431; Tanner, D.; Somfai. P. Tetrahedron, 1988, 44, 619-624.
65. Moulines, J.; Charpentier, P.; Bats, J.-P.; Nuhrich, A.; Lamidey, A.-M. Tetrahedron Lett., 1992, 33, 487-490; see also: Najime, R.; Pilard, S.; Vaultier, M. Tetrahedron Lett., 1992, 33, 5351-5354; Kowollik, W.; Janairo, G.; Voelter, W. Justus Liebigs Ann. Chem., 1988, 427-431; Tanner, D.; Somfai. P. Tetrahedron, 1988, 44, 619-624.
66. Moulines, J.; Charpentier, P.; Bats, J.-P.; Nuhrich, A.; Lamidey, A.-M. Tetrahedron Lett., 1992, 33, 487-490; see also: Najime, R.; Pilard, S.; Vaultier, M. Tetrahedron Lett., 1992, 33, 5351-5354; Kowollik, W.; Janairo, G.; Voelter, W. Justus Liebigs Ann. Chem., 1988, 427-431; Tanner, D.; Somfai. P. Tetrahedron, 1988, 44, 619-624.
67. Wilson, R.J.; Rayner, C.M.; Marchington, A.P.; Monaghan, S.M. unpublished results.
68. Still, W.C.; Khan, M.; Mitra, A. J. Org. Chem., 1978, 43, 2923-2925; see also: Leonard, J.; Lygo, B.; Procter, G. Advanced Practical Chemistry, Blackie, 1990, pp. 204-217.
69. Still, W.C.; Khan, M.; Mitra, A. J. Org. Chem., 1978, 43, 2923-2925; see also: Leonard, J.; Lygo, B.; Procter, G. Advanced Practical Chemistry, Blackie, 1990, pp. 204-217.
70. Perrin, D.D.; Armarego, W.L.F.; Perrin, D.R. Purification of Laboratory Chemicals, Pergamon, 1980.