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Volumn 1, Issue 11, 2003, Pages 1842-1844

An enantioselective double Diels-Alder approach to the tetracyclic framework of colombiasin A

Author keywords

[No Author keywords available]

Indexed keywords

HEATING; REDUCTION; SINGLE CRYSTALS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

EID: 0038264406     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b302522e     Document Type: Article
Times cited : (21)

References (40)
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    • note
    • The name given to the core, dodecahydro-5a,8b-butanoacenaphthylene I, is based on IUPAC nomenclature and has different numbering to the terpenoid colombiane skeleton II, identified by Rodriguez (see ref 1).
  • 3
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    • For a total synthesis of colombiasin A see; (Angew. Chem., Int. Ed., 2001, 40, 2482-2486)
    • For a total synthesis of colombiasin A see: (a) K. C. Nicolaou, G. Vassilikogiannakis, W. Mägerlien and R. Kranich, Angew. Chem., 2001, 113, 2543-2547 (Angew. Chem., Int. Ed., 2001, 40, 2482-2486)
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  • 5
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    • For other synthetic work on colombiasin A see
    • For other synthetic work on colombiasin A see: D. C. Harrowven and M. J. Tyte, Tetrahedron Lett., 2001, 42, 8709-8711.
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    • For recent reviews on the Diels-Alder reaction see; (Angew. Chem., Int. Ed., 2002, 41, 1650-1667)
    • For recent reviews on the Diels-Alder reaction see: (a) E. J. Corey, Angew. Chem., 2002, 114, 1724-1741 (Angew. Chem., Int. Ed., 2002, 41, 1650-1667)
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    • (e) D. A. Evans and J. S. Johnson, in Comprehensive Asymmetric Catalysis, vol. 3, eds E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin, 1999, pp. 1177-1235
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    • eds. B. M. Trost and I. Flemming, Pergamon, Oxford
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    • eds B. M. Trost and I. Flemming, Pergamon, Oxford
    • (i) W. R. Roush, in Comprehensive Organic Synthesis vol. 5, eds B. M. Trost and I. Flemming, Pergamon, Oxford, 1991, 513-550
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    • For reviews on asymmetric Diels-Alder reactions employing chiral sulfoxides see
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    • (c) M. C. Carreño, Chem Rev., 1995, 95, 1717-1760; for selected references see
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    • note
    • This DA-E-IMDA sequences is similar to the "pincer" Diels-Alder reaction, which consists of two Diels-Alder reactions upon the same alkyne see: ref 4b and M. Lautens and E. Fillion, J. Org. Chem., 1997, 62, 4418-4427 and references cited therein.
    • (1997) J. Org. Chem. , vol.62 , pp. 4418-4427
  • 25
    • 0036008841 scopus 로고    scopus 로고
    • For reviews on diversity-orientated synthesis using natural product-like templates see
    • For reviews on diversity-orientated synthesis using natural product-like templates see: (a) P. Arya, R. Joseph and D. T. H. Chou, Chem. Biol., 2002, 9, 145-156 and references cited therein
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    • note
    • -3. CCDC reference number 199385. See http://www.rsc.org/suppdata/ob/b3/b302522e/ for crystallographic data in .cif or other electronic format.
  • 39
    • 0037712590 scopus 로고    scopus 로고
    • note
    • The er was determined using chiral HPLC, this involved the synthesis of racemic 17 using ethyl p-toluenesulfinate in place of 13 in Scheme 4 (see ESI for details†).
  • 40
    • 0038726918 scopus 로고    scopus 로고
    • note
    • †).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.