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Volumn 43, Issue 7, 2004, Pages 895-897

Steroids and steroid analogues from Stille-Heck coupling sequences

Author keywords

Cross coupling; Homogeneous catalysis; Pericyclic reactions; Steroids; Total synthesis

Indexed keywords

REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 4544333057     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200352162     Document Type: Article
Times cited : (41)

References (45)
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  • 11
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    • (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim
    • For reviews on the Stille reaction see: a) T. N. Mitchell in Metal-Catalyzed Cross-Coupling Reactions (Eds.: F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998, pp. 167-202;
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 167-202
    • Mitchell, T.N.1
  • 18
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    • note
    • For the trans-configurated enol triflate the yield was determined over two steps since the diisobutylaluminum enolate was first trapped as the trimethylsilyl enol ether, which was cleaved with MeLi to form the more reactive lithium enolate.
  • 27
    • 4544351137 scopus 로고    scopus 로고
    • note
    • 3 the product trans-4b was obtained in a comparable yield of 84%.
  • 28
    • 0038262764 scopus 로고    scopus 로고
    • Reactions with tert-butyl acrylate proved to give consistently better yields those with methyl acrylate, from which early precipitation of palladium black was observed. This may be attributed to a better stabilization of the palladium(o) catalyst by the less electron-deficient tert-butyl acrylate. Cf. a) M. Buback, T. Perkovic, S. Redlich, A. de Meijere, Eur. J. Org. Chem. 2003, 2375-2382;
    • (2003) Eur. J. Org. Chem. , pp. 2375-2382
    • Buback, M.1    Perkovic, T.2    Redlich, S.3    De Meijere, A.4
  • 29
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    • Dissertation, Universität Göttingen
    • T. Perkovic, Dissertation, Universität Göttingen, 1999.
    • (1999)
    • Perkovic, T.1
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    • 3P: a) W. A. Herrmann, C. Brossmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer, Angew. Chem. 1995, 107, 1989-1992; Angew. Chem. Int. Ed. Engl. 1995, 34, 1844-1848;
    • (1995) Angew. Chem. Int. Ed. Engl. , vol.34 , pp. 1844-1848
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    • d) L. F. Tietze, T. Nöbel, M. Spescha, Angew. Chem. 1996, 108, 2385-2386; Angew. Chem. Int. Ed. Engl. 1996, 35, 2259-2261.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2259-2261
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    • Dissertation, Universität Göttingen
    • b) A. Lansky, Dissertation, Universität Göttingen, 1992.
    • (1992)
    • Lansky, A.1
  • 41
    • 4544283493 scopus 로고    scopus 로고
    • note
    • When the hexatrienes were heated at lower temperatures (150-160°C), the reaction required significantly longer times. For example, even after 12 h traces of the starting materials could be detected and, besides the desired products, several side products were formed.
  • 42
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    • a) B. M. Trost, P. G. McDougal, J. Org. Chem. 1984, 49, 458-468. This rotational selectivity has also been termed torquoselectivity. Cf.
    • (1984) J. Org. Chem. , vol.49 , pp. 458-468
    • Trost, B.M.1    McDougal, P.G.2
  • 45
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    • note
    • 1H NOESY NMR experiments in which interactions within the steroid analogue cis-6b between the protons of the methyl group at C13 and the proton at C14 as well as between the proton at C14 and the proton at C7 were detected. For the steroid trans-8b interactions between the methyl group at C13 and the proton at C8 could be observed, and also interactions between the proton at C7 and the proton at C8 as well as the proton at C14 and one proton at C15 were found.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.