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Volumn 64, Issue 5, 1999, Pages 1657-1666

Probing host-selective phytotoxicity: Synthesis and biological activity of phomalide, isophomalide, and dihydrophomalide

Author keywords

[No Author keywords available]

Indexed keywords

DEPSIPEPTIDE; DIHYDROPHOMALIDE; ISOPHOMALIDE; PHOMALIDE; UNCLASSIFIED DRUG;

EID: 0344061598     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982376p     Document Type: Article
Times cited : (36)

References (101)
  • 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
  • 3
  • 9
    • 0003175687 scopus 로고
    • Gross, E., Meienhofer, J., Eds.; Academic Press: New York
    • (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
  • 18
    • 0032518701 scopus 로고    scopus 로고
    • For examples containing an (E)-Aba residue, see: (i) Sano, T.; Kaya, K. Tetrahedron 1998, 54, 463-870.
    • (1998) Tetrahedron , vol.54 , pp. 463-870
    • Sano, T.1    Kaya, K.2
  • 23
    • 0040562798 scopus 로고    scopus 로고
    • For a recent review on phytotoxins of the blackleg fungus, see: Pedras, M. S. C. Rev. Latinoam. Quim. 1996, 24, 177-182.
    • (1996) Rev. Latinoam. Quim. , vol.24 , pp. 177-182
    • Pedras, M.S.C.1
  • 35
    • 0017783272 scopus 로고
    • and cited references
    • Rich, D. H.; Tam, J. P. J. Org. Chem. 1977, 42, 3815-3820, and cited references.
    • (1977) J. Org. Chem. , vol.42 , pp. 3815-3820
    • Rich, D.H.1    Tam, J.P.2
  • 36
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    • and cited references
    • Somekh, L.; Shanzer, A. J. Org. Chem. 1983, 48, 907-908, and cited references.
    • (1983) J. Org. Chem. , vol.48 , pp. 907-908
    • Somekh, L.1    Shanzer, A.2
  • 45
    • 0344870148 scopus 로고    scopus 로고
    • note
    • 11c,12,17
  • 51
    • 0345301406 scopus 로고    scopus 로고
    • note
    • 2O, bis(1,1-dimethylethyl) dicarbonate; BOP, (1H-benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; BOP-Cl, N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride; CSA, 10-camphorsulfonic acid; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DCC, dicyclohexylcarbodiimide; DEAD, diethyl azodicarboxylate; DMAP, 4-(dimethylamino)pyridine; DPPA, diphenylphosphoryl azide; EDC, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride; FDPP, pentafluorophenyl diphenylphosphinate; HOBt, 1-hydroxybenzotriazole; TFA, trifluoroacetic acid.
  • 52
    • 0344870146 scopus 로고    scopus 로고
    • note
    • 23
  • 60
    • 0344438322 scopus 로고    scopus 로고
    • note
    • 2O gave 14 of 80% ee as determined by optical rotation. That 80% ee is the minimum enantiopurity of 5 is further supported by obtention of (Z)-15 and (E)-15 in >90% combined yield; other diastereomers were not detected.
  • 63
    • 0010580051 scopus 로고
    • 1H NMR on the basis of the well-documented trend that the chemical shifts for the vinyl proton, the vinyl methyl group, and the enamine N-H are at lower fields in the (E)-isomers than in the (Z)-isomers. For example, see: (a) Srinivasan, A.; Richards, K. D.; Olsen, R. K. Tetrahedron Lett. 1976, 891-894.
    • (1976) Tetrahedron Lett. , pp. 891-894
    • Srinivasan, A.1    Richards, K.D.2    Olsen, R.K.3
  • 79
    • 0345301401 scopus 로고    scopus 로고
    • note
    • C < 0.5).
  • 80
    • 0344870143 scopus 로고    scopus 로고
    • note
    • Retention times for 1 and 2 were 30.4 and 29.8 min, respectively, with a hypersil ODS column (5-μm particle size; 4.6 × 200 mm) using MeCN/water gradient elution (1 mL/min; 25-75% MeCN over 35 min).
  • 81
    • 0344007028 scopus 로고    scopus 로고
    • note
    • 2; benzene/ ether/acetone, 90:5:5) of a 10:1 mixture of (Z)-15 and (E)-15.
  • 86
    • 0015242312 scopus 로고
    • For other examples of dehydroamino acid syntheses by selenoxide fragmentation, see: (a) Walter, R.; Roy, J. J. Org. Chem. 1971, 36, 2561-6563.
    • (1971) J. Org. Chem. , vol.36 , pp. 2561-6563
    • Walter, R.1    Roy, J.2
  • 89
    • 0344870140 scopus 로고    scopus 로고
    • note
    • Phomalide and isophomalide are separable (PTLC; 30% ethyl acetate in hexane, multiple development), albeit with considerable difficulty (phomalide is slightly less polar) and with low efficiency (i.e., mainly mixed fractions are obtained).
  • 90
    • 0345301400 scopus 로고    scopus 로고
    • note
    • Obtained in 90% yield from 10 and (2R)-2-hydroxy-3-phenylpropanoic acid in analogy to the preparation of 6.
  • 94
    • 0344438317 scopus 로고    scopus 로고
    • note
    • f = 0.26.
  • 97
    • 0344438314 scopus 로고    scopus 로고
    • Unpublished results
    • Addition of PhSeH to Aba residues in acyclic peptides also gives the like diastereomer selectively. For example reactions of Val-(Z)-Aba-Hpp-Hmp derivatives with PhSeH/BuLi followed by oxidation gave the corresponding (E)-isomers with ca. 5:1 diastereoselectivity (Ward, D. E.; Vázquez, A. Unpublished results).
    • Ward, D.E.1    Vázquez, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.