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Volumn 64, Issue 3, 1999, Pages 914-924

A unified strategy toward the synthesis of acerogenin-type macrocycles: Total syntheses of acerogenins A, B, C, and L and aceroside IV

Author keywords

[No Author keywords available]

Indexed keywords

ACEROGENIN A; ACEROGENIN B; ACEROGENIN C; ACEROGENIN L; ACEROSIDE 4; UNCLASSIFIED DRUG;

EID: 0344076297     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981844s     Document Type: Article
Times cited : (62)

References (80)
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    • (1995) Studies in Natural Products Chemistry , vol.17 , pp. 357-394
    • Keserü, G.M.1    Nógrádi, M.2
  • 25
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    • note
    • The oxidative coupling of phenol promoted by thallium tris-(trifluoroacetate) has been reported to give macrocyclic biaryl ether in nonspecified yield. See ref 10.
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    • (a) Zhu, J. Synlett 1997, 133-144.
    • (1997) Synlett , pp. 133-144
    • Zhu, J.1
  • 38
    • 0030773677 scopus 로고    scopus 로고
    • Syntheses of acerogenin C and aceroside IV have been described in a preliminary communication: Islas Gonzalez, G.; Zhu, J. J. Org. Chem. 1997, 62, 7544-7545.
    • (1997) J. Org. Chem. , vol.62 , pp. 7544-7545
    • Islas Gonzalez, G.1    Zhu, J.2
  • 49
    • 0344935512 scopus 로고    scopus 로고
    • note
    • A mixture of cyclic and noncyclic dimers was also isolated, which accounts for the total mass balance of the reaction.
  • 53
    • 0344504730 scopus 로고    scopus 로고
    • note
    • We thank Professor Nagai for kindly sending us the NMR spectra of natural acerogenin C and aceroside IV.
  • 54
    • 0344935511 scopus 로고    scopus 로고
    • note
    • One of the reviewers pointed out that hindered rotation of the para-disubstituted aromatic ring cannot be excluded in acerogenin A. The lack of anisochrony can be attributed to the absence of any of the following three effects: (1) hindered rotation of the aromatic ring; (2) hindered interconversion of planary chiral conformations associated with the flipping of the seven-membered chain; (3) the center of chirality at C-12. Note that the second effect interconverts in the case of acerogenin A enantiomers while it does not in the case of acerogenin C diastereomers.
  • 67
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    • (c) Nicolaou, K. C.; Yang, Z.; Liu, J.-J.; Nantermet, P. G.; Claiborne, C. F.; Renaud, J.; Guy, R. K.; Shibayama, K. J. Am. Chem. Soc. 1995, 117, 645-852. The term "Protecting Group Tuning Effect" was originary proposed by Reetz to account for the diastereoselectivity dependence on the neighboring protecting group (Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531).
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1531
  • 73
    • 0344504728 scopus 로고    scopus 로고
    • note
    • For molecular modeling studies on similar substrates, see ref 18.
  • 78
  • 80
    • 0345366912 scopus 로고    scopus 로고
    • note
    • 13C NMR, elemental analysis and HRMS) are in accord with the structural assignment of 43 and 44, the planar chiralities of these two compounds were not thoroughly determined. The physical data described in the Experimental Section were arbitrary assigned for 43 and 44.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.