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1
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For a recent multiauthor review on phytotoxins, see: Graniti, A.; et al. Experientia 1991, 47, 751-826.
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Experientia
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Graniti, A.1
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2
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(a) For a recent review on the history and control of blackleg disease, see: Gugel, R. K.; Petrie, G. A. Can. J. Plant Pathol. 1992, 14, 36-45.
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Gugel, R.K.1
Petrie, G.A.2
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3
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4243082495
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note
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(b) Canola refers to varieties of rapeseed containing very low amounts of erucic adic and glucosinolates.
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4
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17444416686
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Pedras, M. S. C.; Taylor, J. T.; Nakashima, T. T. J. Org. Chem. 1993, 58, 4778-4780.
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Pedras, M.S.C.1
Taylor, J.T.2
Nakashima, T.T.3
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Halsted Press: New York
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(b) Izumiya, N.; Kato, T.; Aoyagi, H.; Waki, M.; Kondo, M. Synthetic Aspects of Biologically Acitve Cyclic Peptides; Halsted Press: New York, 1979.
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Synthetic Aspects of Biologically Acitve Cyclic Peptides
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Izumiya, N.1
Kato, T.2
Aoyagi, H.3
Waki, M.4
Kondo, M.5
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11
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0023872535
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Reviews: (a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159-172. (b) Noda, K.; Shimohigashi, Y.; Izumiya, N. In The Peptides; Gross, E.; Meienhofer, J., Eds.; Academic Press: New York, 1983, Vol. 5, pp 285-339.
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Synthesis
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Schmidt, U.1
Lieberknecht, A.2
Wild, J.3
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12
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0003175687
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Gross, E.; Meienhofer, J., Eds.; Academic Press: New York
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Reviews: (a) Schmidt, U.; Lieberknecht, A.; Wild, J. Synthesis 1988, 159-172. (b) Noda, K.; Shimohigashi, Y.; Izumiya, N. In The Peptides; Gross, E.; Meienhofer, J., Eds.; Academic Press: New York, 1983, Vol. 5, pp 285-339.
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The Peptides
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Noda, K.1
Shimohigashi, Y.2
Izumiya, N.3
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13
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0017783272
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7 The (E)-isomers can be prepared by syn-elimination of certain threonine derivatives [(a) Rich, D. H.; Tam, J. P. J. Org. Chem. 1977, 42, 3815-3820] or by anti-elimination of allo-threonine derivatives: (b) Somekh, L.; Shanzer, A. Ibid. 1983, 48, 907-908 and cited references.
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J. Org. Chem.
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Rich, D.H.1
Tam, J.P.2
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14
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0001392262
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and cited references
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7 The (E)-isomers can be prepared by syn-elimination of certain threonine derivatives [(a) Rich, D. H.; Tam, J. P. J. Org. Chem. 1977, 42, 3815-3820] or by anti-elimination of allo-threonine derivatives: (b) Somekh, L.; Shanzer, A. Ibid. 1983, 48, 907-908 and cited references.
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J. Org. Chem.
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, pp. 907-908
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Somekh, L.1
Shanzer, A.2
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15
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0029785860
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For a recent example involving (Z)-Aba, see: Li, K. W.; Wu, J.; Xing, W.; Simon, J. A. J. Am. Chem. Soc. 1996, 118, 7237-7238.
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J. Am. Chem. Soc.
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Li, K.W.1
Wu, J.2
Xing, W.3
Simon, J.A.4
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16
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0004639678
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(a) Cavelier-Frontin, F.; Achmad, S.; Verducci, J.; Jacquier, J.; Pèpe, G. J. Mol. Struct. (THEOCHEM) 1993, 286, 125-130.
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J. Mol. Struct. (THEOCHEM)
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Cavelier-Frontin, F.1
Achmad, S.2
Verducci, J.3
Jacquier, J.4
Pèpe, G.5
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17
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0023377546
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and cited references
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(b) Ueda, K.; Waki, M.; Izumiya, N. Int. J. Pept. Protein Res. 1987, 30, 33-39 and cited references.
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Int. J. Pept. Protein Res.
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Ueda, K.1
Waki, M.2
Izumiya, N.3
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18
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85087247570
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note
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6
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19
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4243126277
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note
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The Aba-Hpp linkage is also an attractive cyclization site because it is not subject to "racemization".
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20
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0000531237
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(a) Nitz, T. J.; Holt, E. M.; Rubin, B.; Stammer, C. H. J. Org. Chem. 1981, 46, 2667-2673.
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Nitz, T.J.1
Holt, E.M.2
Rubin, B.3
Stammer, C.H.4
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21
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0001852179
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(b) Arenal, I.; Bernabe, M.; Fernadez-Alvarez, E. An. Quim., Ser. C 1981, 77, 56-62.
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An. Quim., Ser. C
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Arenal, I.1
Bernabe, M.2
Fernadez-Alvarez, E.3
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22
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84985180861
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(c) Makowski, M.; Rzezotarska, B.; Kubica, Z.; Pietrzynski, G.; Hetper, J. Liebigs Ann. Chem. 1986, 980-991.
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Liebigs Ann. Chem.
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Makowski, M.1
Rzezotarska, B.2
Kubica, Z.3
Pietrzynski, G.4
Hetper, J.5
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25
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84912953797
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(a) Makowski, M.; Rzeszotarska, B.; Kubica, Z.; Wieczorek, P. Liebigs Ann. Chem. 1984, 920-928.
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Liebigs Ann. Chem.
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Makowski, M.1
Rzeszotarska, B.2
Kubica, Z.3
Wieczorek, P.4
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26
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84913008816
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(b) Smelka, L.; Rzeszotarska, B.; Pietrznski, G.; Kubica, Z. Liebigs Ann. Chem. 1988, 485-486.
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Smelka, L.1
Rzeszotarska, B.2
Pietrznski, G.3
Kubica, Z.4
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27
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4243162614
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note
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A small amount of the corresponding (E)-isomer (ca. 5%) could be isolated. A similar result was obtained starting from either the pure (E)- or pure (Z)-isomer of 3.
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-
-
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29
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4243153278
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note
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Cyclization of the (E)-isomer of 13 under the same conditions gave a mixture of 1 and 2 in good yield.
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-
-
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30
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0039969912
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Rich, D. H., Gross, E., Eds.; Pierce Chem. Co.: Rockford, IL
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(a) Mazur, R. H.; Pilipauskas, D. R. Pept.: Synth, Struct., Funct., Proc. Am. Pept. Symp., 7th; Rich, D. H., Gross, E., Eds.; Pierce Chem. Co.: Rockford, IL, 1981; pp 81-84.
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Pept.: Synth, Struct., Funct., Proc. Am. Pept. Symp., 7th
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Mazur, R.H.1
Pilipauskas, D.R.2
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31
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0041156873
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Blaha, K., Malon, P., Eds.; de Gruyter: Berlin
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(b) Mazur, R. H.; Pilipauskas, D. R. Pept., Proc. Eur. Pept. Symp., 17th; 1982; Blaha, K., Malon, P., Eds.; de Gruyter: Berlin, 1983; pp 319-322.
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Pept., Proc. Eur. Pept. Symp., 17th; 1982
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Mazur, R.H.1
Pilipauskas, D.R.2
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32
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4243123368
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note
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Similar oxidation of the minor selenide isomer gave a 6:1 mixture of 1 and 2; oxidation of the other isomer gave only 2. Thus, assuming a stereoselective syn elimination of the selenides (via the corresponding selenoxides), the relative stereochemistry for major and minor isomers should be lk (i.e., syn PhSe and NH groups) and ul for the second major isomer. Phomalide and isophomalide are separable (PTLC), albeit with considerable difficulty and with low efficiency (i.e., mainly mixed fractions are obtained).
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-
-
-
33
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0015242312
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For a similar syn-elimination of sulfoxide derivatives of threonine, see ref 8a. For other examples of dehydroamino acid syntheses by selenoxide fragmentation, see: (a) Walter, R.; Roy, J. J. Org. Chem. 1971, 36, 2561-6563. (b) Reich, H. J.; Jasperse, C. P.; Renga, J. M. Ibid. 1986, 51, 2981-2988. (c) Hashimoto, K.; Sakai, M.; Okuno, T.; Shirahama, H. Chem. Commun. 1996, 1139-1140.
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J. Org. Chem.
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Walter, R.1
Roy, J.2
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34
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0013295010
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For a similar syn-elimination of sulfoxide derivatives of threonine, see ref 8a. For other examples of dehydroamino acid syntheses by selenoxide fragmentation, see: (a) Walter, R.; Roy, J. J. Org. Chem. 1971, 36, 2561-6563. (b) Reich, H. J.; Jasperse, C. P.; Renga, J. M. Ibid. 1986, 51, 2981-2988. (c) Hashimoto, K.; Sakai, M.; Okuno, T.; Shirahama, H. Chem. Commun. 1996, 1139-1140.
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J. Org. Chem.
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Reich, H.J.1
Jasperse, C.P.2
Renga, J.M.3
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35
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1542682080
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For a similar syn-elimination of sulfoxide derivatives of threonine, see ref 8a. For other examples of dehydroamino acid syntheses by selenoxide fragmentation, see: (a) Walter, R.; Roy, J. J. Org. Chem. 1971, 36, 2561-6563. (b) Reich, H. J.; Jasperse, C. P.; Renga, J. M. Ibid. 1986, 51, 2981-2988. (c) Hashimoto, K.; Sakai, M.; Okuno, T.; Shirahama, H. Chem. Commun. 1996, 1139-1140.
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Chem. Commun.
, pp. 1139-1140
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Hashimoto, K.1
Sakai, M.2
Okuno, T.3
Shirahama, H.4
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36
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85087250725
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note
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D, TLC and HPLC retention times) with an authentic sample.
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37
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0029108893
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Pedras, M. S. C.; Taylor, J. L.; Morales, V. M. Phytochemistry 1995, 38, 1215-1222.
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Phytochemistry
, vol.38
, pp. 1215-1222
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Pedras, M.S.C.1
Taylor, J.L.2
Morales, V.M.3
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38
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0000751777
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Pedras, M. S. C.; Séguin-Swartz, G.; Abrams, S. R. Phytochemistry 1990, 29, 777-782.
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Phytochemistry
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Pedras, M.S.C.1
Séguin-Swartz, G.2
Abrams, S.R.3
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