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Volumn 61, Issue 23, 1996, Pages 8008-8009

Understanding host-selective phytotoxicity: Synthesis and biological discrimination of phomalide and its (Z)-isomer

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EID: 0006386142     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961661a     Document Type: Article
Times cited : (21)

References (38)
  • 1
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    • For a recent multiauthor review on phytotoxins, see: Graniti, A.; et al. Experientia 1991, 47, 751-826.
    • (1991) Experientia , vol.47 , pp. 751-826
    • Graniti, A.1
  • 2
    • 0002930751 scopus 로고
    • (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.
    • (1992) Can. J. Plant Pathol. , vol.14 , pp. 36-45
    • Gugel, R.K.1    Petrie, G.A.2
  • 3
    • 4243082495 scopus 로고    scopus 로고
    • note
    • (b) Canola refers to varieties of rapeseed containing very low amounts of erucic adic and glucosinolates.
  • 11
    • 0023872535 scopus 로고
    • 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.
    • (1988) Synthesis , pp. 159-172
    • Schmidt, U.1    Lieberknecht, A.2    Wild, J.3
  • 12
    • 0003175687 scopus 로고
    • Gross, E.; Meienhofer, J., Eds.; Academic Press: New York
    • 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.
    • (1983) The Peptides , vol.5 , pp. 285-339
    • Noda, K.1    Shimohigashi, Y.2    Izumiya, N.3
  • 13
    • 0017783272 scopus 로고
    • 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.
    • (1977) J. Org. Chem. , vol.42 , pp. 3815-3820
    • Rich, D.H.1    Tam, J.P.2
  • 14
    • 0001392262 scopus 로고
    • and cited references
    • 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.
    • (1983) J. Org. Chem. , vol.48 , pp. 907-908
    • Somekh, L.1    Shanzer, A.2
  • 18
    • 85087247570 scopus 로고    scopus 로고
    • note
    • 6
  • 19
    • 4243126277 scopus 로고    scopus 로고
    • note
    • The Aba-Hpp linkage is also an attractive cyclization site because it is not subject to "racemization".
  • 27
    • 4243162614 scopus 로고    scopus 로고
    • note
    • 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.
  • 29
    • 4243153278 scopus 로고    scopus 로고
    • note
    • Cyclization of the (E)-isomer of 13 under the same conditions gave a mixture of 1 and 2 in good yield.
  • 32
    • 4243123368 scopus 로고    scopus 로고
    • note
    • 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).
  • 33
    • 0015242312 scopus 로고
    • 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.
    • (1971) J. Org. Chem. , vol.36 , pp. 2561-6563
    • Walter, R.1    Roy, J.2
  • 34
    • 0013295010 scopus 로고
    • 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.
    • (1986) J. Org. Chem. , vol.51 , pp. 2981-2988
    • Reich, H.J.1    Jasperse, C.P.2    Renga, J.M.3
  • 35
    • 1542682080 scopus 로고    scopus 로고
    • 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.
    • (1996) Chem. Commun. , pp. 1139-1140
    • Hashimoto, K.1    Sakai, M.2    Okuno, T.3    Shirahama, H.4
  • 36
    • 85087250725 scopus 로고    scopus 로고
    • note
    • D, TLC and HPLC retention times) with an authentic sample.


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