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Volumn 64, Issue 22, 1999, Pages 8275-8280

Total synthesis and structural refinement of the cyclic tripyrrole pigment nonylprodigiosin

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; NONYLPRODIGIOSIN; PALLADIUM; PIGMENT; PYRROLE DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

EID: 0038590297     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991021i     Document Type: Article
Times cited : (172)

References (89)
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    • note
    • 1 phase, mostly downstream from the interaction of IL-2 with its receptor, cf. ref 5.
  • 34
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    • note
    • These different mechanisms of action also suggest that a combined use of these drugs may be possible, permitting the use of relatively low concentrations of each drug and thereby potentially reducing toxicity, cf. ref 5.
  • 35
    • 0344301689 scopus 로고    scopus 로고
    • note
    • 50 of 1 was reported to be 1.5 mg/kg i.p. for 6 days, while toxic signs are appreciable from a dose of 4mg/kg, cf. ref 5.
  • 40
    • 0037644400 scopus 로고    scopus 로고
    • (b) For a synthesis of the structurally related alkaloid roseophilin see: Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 2817
    • Fürstner, A.1    Weintritt, H.2
  • 44
    • 0032580376 scopus 로고    scopus 로고
    • For recent reviews on RCM see the following for leading references: (a) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
    • (1998) Tetrahedron , vol.54 , pp. 4413
    • Grubbs, R.H.1    Chang, S.2
  • 48
    • 0038206375 scopus 로고    scopus 로고
    • For RCM-based macrocycle syntheses from our laboratory see: (a) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942.
    • (1996) J. Org. Chem. , vol.61 , pp. 3942
    • Fürstner, A.1    Langemann, K.2
  • 58
    • 0002437895 scopus 로고    scopus 로고
    • For RCM-based total syntheses of natural products from other groups see the following for leading references: (a) Nicolaou, K. C.; King, N. B.; He, Y. Top. Organomet. Chem. 1998, 1, 73.
    • (1998) Top. Organomet. Chem. , vol.1 , pp. 73
    • Nicolaou, K.C.1    King, N.B.2    He, Y.3
  • 73
    • 2042507954 scopus 로고
    • Review: (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. For recent applications of Suzuki reactions from our laboratory see:
    • (1995) Chem. Rev. , vol.95 , pp. 2457
    • Miyaura, N.1    Suzuki, A.2
  • 80
    • 33750595439 scopus 로고    scopus 로고
    • 2OH is the diphenylallenylidene complex 19, cf. Harlow, K. J.; Hill, A. F.; Winton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285, More detailed studies, however, have shown that the stable product formed is the rearranged product, i.e., the indenylidene ruthenium complex 20, cf. Hill, A. F.; Fürstner, A.; Liebl, M.; Mynott, R.; Gabor, B., Nolan, S. P. Manuscript in preparation.
    • (1999) J. Chem. Soc., Dalton Trans. , pp. 285
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  • 81
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    • Manuscript in preparation
    • 2OH is the diphenylallenylidene complex 19, cf. Harlow, K. J.; Hill, A. F.; Winton-Ely, J. D. E. T. J. Chem. Soc., Dalton Trans. 1999, 285, More detailed studies, however, have shown that the stable product formed is the rearranged product, i.e., the indenylidene ruthenium complex 20, cf. Hill, A. F.; Fürstner, A.; Liebl, M.; Mynott, R.; Gabor, B., Nolan, S. P. Manuscript in preparation.
    • Hill, A.F.1    Fürstner, A.2    Liebl, M.3    Mynott, R.4    Gabor, B.5    Nolan, S.P.6
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    • note
    • One recrystallization provides pure (E)-18 which was used for the X-ray analysis.
  • 88
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    • note
    • 2 = 0.234. For further information, see the Supporting Information. The complete set of data has been deposited at the Cambridge Crystallographic Data Center, Cambridge, UK, under the deposition number CCDC 121761.
  • 89
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    • note
    • The disorder originates from a 2-fold rotation of the macrocycle around an axis passing through the N-atom of the central pyrrole ring.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.