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Volumn 59, Issue 48, 2003, Pages 9609-9617

A practical semi-synthesis of tautomycin using a hydrolysate of natural tautomycin

Author keywords

Inhibitor; Proteinphosphatase; Synthesis; Tautomycin

Indexed keywords

TAUTOMYCIN;

EID: 0242352601     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.097     Document Type: Article
Times cited : (8)

References (45)
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    • For Oikawa and Ichihara's total synthesis, see: (a) Oikawa M., Oikawa H., Ueno T., Ichihara A. Tetrahedron Lett. 30:1993;4797-4800 (b) Oikawa H., Oikawa M., Ueno T., Ichihara A. Tetrahedron Lett. 35:1994;4809-4812 (c) Oikawa M., Ueno T., Oikawa H., Ichihara A. J. Org. Chem. 60:1995;5048-5068 (d) Ueno T., Oikawa M., Oikawa H., Ichihara A. Biosci. Biotech. Biochem. 59:1995;2104-2110. For their group's structure-activity investigations, see: (e) Kawamura T., Matsuzawa S., Mizuno Y., Kikuchi K., Oikawa H., Oikawa M., Ubukata M., Ichihara A. Biochem. Pharmacol. 55:1998;995-1003 (f) Oikawa H. Curr. Med. Chem. 9:2002;2033-2054.
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    • 0032055256 scopus 로고    scopus 로고
    • For Oikawa and Ichihara's total synthesis, see: (a) Oikawa M., Oikawa H., Ueno T., Ichihara A. Tetrahedron Lett. 30:1993;4797-4800 (b) Oikawa H., Oikawa M., Ueno T., Ichihara A. Tetrahedron Lett. 35:1994;4809-4812 (c) Oikawa M., Ueno T., Oikawa H., Ichihara A. J. Org. Chem. 60:1995;5048-5068 (d) Ueno T., Oikawa M., Oikawa H., Ichihara A. Biosci. Biotech. Biochem. 59:1995;2104-2110. For their group's structure-activity investigations, see: (e) Kawamura T., Matsuzawa S., Mizuno Y., Kikuchi K., Oikawa H., Oikawa M., Ubukata M., Ichihara A. Biochem. Pharmacol. 55:1998;995-1003 (f) Oikawa H. Curr. Med. Chem. 9:2002;2033-2054.
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    • Kawamura, T.1    Matsuzawa, S.2    Mizuno, Y.3    Kikuchi, K.4    Oikawa, H.5    Oikawa, M.6    Ubukata, M.7    Ichihara, A.8
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    • 0036034244 scopus 로고    scopus 로고
    • For Oikawa and Ichihara's total synthesis, see: (a) Oikawa M., Oikawa H., Ueno T., Ichihara A. Tetrahedron Lett. 30:1993;4797-4800 (b) Oikawa H., Oikawa M., Ueno T., Ichihara A. Tetrahedron Lett. 35:1994;4809-4812 (c) Oikawa M., Ueno T., Oikawa H., Ichihara A. J. Org. Chem. 60:1995;5048-5068 (d) Ueno T., Oikawa M., Oikawa H., Ichihara A. Biosci. Biotech. Biochem. 59:1995;2104-2110. For their group's structure-activity investigations, see: (e) Kawamura T., Matsuzawa S., Mizuno Y., Kikuchi K., Oikawa H., Oikawa M., Ubukata M., Ichihara A. Biochem. Pharmacol. 55:1998;995-1003 (f) Oikawa H. Curr. Med. Chem. 9:2002;2033-2054.
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    • 0000506770 scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1993) Synlett , pp. 737-738
    • Ichikawa, Y.1    Naganawa, A.2    Isobe, M.3
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    • 0000506769 scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1993) Synlett , pp. 907-908
    • Ichikawa, Y.1    Tsuboi, K.2    Naganawa, A.3    Isobe, M.4
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    • 0028025164 scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1994) Tetrahedron , vol.50 , pp. 8969-8982
    • Naganawa, A.1    Ichikawa, Y.2    Isobe, M.3
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    • 85037469028 scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1995) Synlett , vol.3 , pp. 285-288
    • Jiang, Y.M.1    Ichikawa, Y.2    Isobe, M.3
  • 21
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    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
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    • Ichikawa, Y.1    Tsouboi, K.2    Jiang, Y.3    Naganawa, A.4    Isobe, M.5
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    • 0030057561 scopus 로고    scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1996) Tetrahedron , vol.52 , pp. 2877-2892
    • Jiang, Y.1    Isobe, M.2
  • 23
    • 0030900925 scopus 로고    scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1997) Tetrahedron , vol.53 , pp. 5083-5102
    • Tsuboi, K.1    Ichikawa, Y.2    Naganawa, A.3    Isobe, M.4    Ubukata, M.5    Isono, K.6
  • 24
    • 0030897973 scopus 로고    scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1997) Tetrahedron , vol.53 , pp. 5103-5122
    • Jiang, Y.1    Ichikawa, Y.2    Isobe, M.3
  • 25
    • 0030956226 scopus 로고    scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1997) Tetrahedron , vol.53 , pp. 5123-5142
    • Tsouboi, K.1    Ichikawa, Y.2    Jiang, Y.3    Naganawa, A.4    Isobe, M.5
  • 26
    • 0030035016 scopus 로고    scopus 로고
    • For Isobe's total synthesis, see: (a) Ichikawa Y., Naganawa A., Isobe M. Synlett. 1993;737-738 (b) Ichikawa Y., Tsuboi K., Naganawa A., Isobe M. Synlett. 1993;907-908 (c) Naganawa A., Ichikawa Y., Isobe M. Tetrahedron. 50:1994;8969-8982 (d) Jiang Y.M., Ichikawa Y., Isobe M. Synlett. 3:1995;285-288 (e) Ichikawa Y., Tsouboi K., Jiang Y., Naganawa A., Isobe M. Tetrahedron Lett. 36:1995;7101-7104 (f) Jiang Y., Isobe M. Tetrahedron. 52:1996;2877-2892 (g) Tsuboi K., Ichikawa Y., Naganawa A., Isobe M., Ubukata M., Isono K. Tetrahedron. 53:1997;5083-5102 (h) Jiang Y., Ichikawa Y., Isobe M. Tetrahedron. 53:1997;5103-5122 (i) Tsouboi K., Ichikawa Y., Jiang Y., Naganawa A., Isobe M. Tetrahedron. 53:1997;5123-5142. For his group's structure-activity investigations, see: (j) Sugiyama Y., Ohtani I.I., Isobe M., Takai A., Ubukata M., Isono K. Bioorg. Med. Chem. Lett. 6:1996;3-8 (k) Takai A., Tsuboi K., Koyasu M., Isobe M. Biochem. J. 350:2000;81-88.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 3-8
    • Sugiyama, Y.1    Ohtani, I.I.2    Isobe, M.3    Takai, A.4    Ubukata, M.5    Isono, K.6
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    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1597-1600
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  • 32
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    • For Chamberlin's total synthesis, see: (a) Sheppeck J.E. II, Liu W., Chamberlin A.R. J. Org. Chem. 62:1997;387-398. For his group's structure-activity investigations, see: (b) Liu W., Sheppeck J.E. II, Colby D.A., Huang H.-B., Nairn A.C., Chamberlin A.R. Bioorg. Med. Chem. Lett. 13:2003;1597-1600 (c) Colby D.A., Liu W., Sheppeck J.E. II, Huang H.-B., Nairn A.C., Chamberlin A.R. Bioorg. Med. Chem. Lett. 13:2003;1601-1605.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1601-1605
    • Colby, D.A.1    Liu, W.2    Sheppeck J.E. II3    Huang, H.-B.4    Nairn, A.C.5    Chamberlin, A.R.6
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    • Synthesis of the C1-C21 subunit of tautomycin: a formal total synthesis Marshall J.A., Yanik M.M. J. Org. Chem. 66:2001;1373-1379.
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    • Marshall, J.A.1    Yanik, M.M.2


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