An access to (Z)-ethylenic pseudodipeptides based on ring-closing metathesis

Tetrahedron

Volumn 58, Issue 36, 2002, Pages 7275-7290

  Boucard, Valérie ^a   Sauriat Dorizon, Hélène ^a   Guibé, François ^a  

^a UNIVERSITÉ PARIS SUD   (France)

Author keywords

(olefin) metathesis; (Z ethylenic) pseudopeptides; Peptidomimetics; Ring closing metathesis

Indexed keywords

[N (METHYL)LEUCYL]GLYCINE; [N (METHYL)LEUCYL]LEUCINE; ALKENE; AMIDE; AMINO ACID; AMINO ACID DERIVATIVE; ANILINE; DIHYDROPYRIDINE; DIPYRONE; ETHYLENE; GLYCINE; PSEUDOPEPTIDE; RUTHENIUM; UNCLASSIFIED DRUG; VALINE;

AMINO ACID SUBSTITUTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DEGRADATION; ENANTIOMER; HYDROLYSIS; PRIORITY JOURNAL; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0037008927     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00795-0     Document Type: Article

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69. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
70. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
71. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
72. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
73. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
74. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
75. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
76. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
77. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.
78. For lists of publications concerning the synthesis of E-alkenyl pseudopeptides up to mid-1994, see Ref. 2b and (a) Ibuka T., Mimura N., Aoyama H., Akaji M., Ohno H., Miwa Y., Taga T., Nakai K., Tamamura H., Fujii N.J. Org. Chem. 62:1997;999-1015 (b) Lehman de Gaeta L.S., Czarniecki M., Spaltenstein A. J. Org. Chem. 54:1989;4004-4005. and references cited therein © Daly M.J., Ward R.A., Thompson D.F., Procter G. Tetrahedron Lett. 36:1995;7545-7548. and 7549-7550 (d) Whitesell J.K., Lawrence R.M. Chirality. 1:1989;89-91 (e) McKinney J.A., Eppley D.F., Keenan R.M. Tetrahedron Lett. 35:1994;5995-5998 (f) Yong Y.F., Lipton M.A. Bioorg. Med. Chem. Lett. 3:1993;2879-2882 (g) Wai J.S., Fisher T.E., Embrey M.W. Tetrahedron Lett. 36:1995;3461-3464 (h) Imogai H., Petit Y., Larchevêque M. Synlett. 1997;615-617 (i) Ibuka T., Habashita H., Otaka A., Fujii N., Garrido F., Mann A., Chounan A., Yamamoto Y.J. Org. Chem. 56:1991;4370-4382. and references cited therein (j) Ibuka T., Mimura N., Ohno H., Nakai K., Akaji M., Habashita H., Tamamura H., Miwa Y., Taga T., Fujii N.J. Org. Chem. 62:1997;2982-2991. and references cited therein (k) Beresis R., Panek J. Bioorg. Med. Chem. Lett. 3:1993;1609-1614 (l) Masse C.E., Knight B.S., Stavropoulos P., Panek J.S. J. Am. Chem. Soc. 119:1997;6040-6047.