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Volumn 129, Issue 40, 2007, Pages 12320-12327

An expedient formal total synthesis of (-)-diazonamide A via a powerful, stereoselective O-aryl to C-aryl migration to form the C10 quaternary center

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONAMIDE; STEREOISOMERS; TRYPTOPHAN; TYROSINE;

EID: 35248823162     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0744448     Document Type: Article
Times cited : (72)

References (74)
  • 37
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    • Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; H, X.; Chen, D. Y.-K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753-1758.
    • (b) Nicolaou, K. C.; Rao, P. B.; Hao, J.; Reddy, M. V.; Rassias, G.; H, X.; Chen, D. Y.-K.; Snyder, S. A. Angew. Chem., Int. Ed. 2003, 42, 1753-1758.
  • 52
    • 35248820054 scopus 로고    scopus 로고
    • The Nicolaou synthesis reduces 20 to the derived alcohol and selectively O-benzylates (J. Am. Chem. Soc. 2004, 126, 12888-12896, Scheme 6, p 12893). Neither NaHMDS nor LiHMDS worked in our hands; consequently, we examined maintaining the carboxylate oxidation level through the direct use of 21 and the formation of the trianion 21a.
    • The Nicolaou synthesis reduces 20 to the derived alcohol and selectively O-benzylates (J. Am. Chem. Soc. 2004, 126, 12888-12896, Scheme 6, p 12893). Neither NaHMDS nor LiHMDS worked in our hands; consequently, we examined maintaining the carboxylate oxidation level through the direct use of 21 and the formation of the trianion 21a.
  • 53
    • 0032079608 scopus 로고    scopus 로고
    • For references to azaxylylene intermediates formed from 1,4-elimination, see
    • For references to azaxylylene intermediates formed from 1,4-elimination, see: Ly, T.-M.; Laso, N. M.; Zard, S. Z. Tetrahedron 1998, 54, 4889-4898.
    • (1998) Tetrahedron , vol.54 , pp. 4889-4898
    • Ly, T.-M.1    Laso, N.M.2    Zard, S.Z.3
  • 58
    • 35248892326 scopus 로고    scopus 로고
    • Bould, L. Studies on the synthesis of tetracycline. Ph.D. Thesis; Imperial College, London, 1968; pp 91 and 153. In the above thesis, the conversion of 56 into 57 is described. The text (p 93) describes the yield of 57 as 20%. However, the experimental section (p 153) converts 56 (125 mg) into 57 (37 mg), corresponding to a 29.6% yield. In 1968, Magnus was a Ph.D. student working next to Bould, and as a consequence knew about the transformation of 56 into 57. This information initiated the notion (36 years later!) that this type of reaction could be used for the construction of the C-10 quaternary center in diazonamide A. (Chemical Equation Presented)
    • Bould, L. Studies on the synthesis of tetracycline. Ph.D. Thesis; Imperial College, London, 1968; pp 91 and 153. In the above thesis, the conversion of 56 into 57 is described. The text (p 93) describes the yield of 57 as 20%. However, the experimental section (p 153) converts 56 (125 mg) into 57 (37 mg), corresponding to a 29.6% yield. In 1968, Magnus was a Ph.D. student working next to Bould, and as a consequence knew about the transformation of 56 into 57. This information initiated the notion (36 years later!) that this type of reaction could be used for the construction of the C-10 quaternary center in diazonamide A. (Chemical Equation Presented)
  • 62
    • 66249126171 scopus 로고
    • A spontaneous reaction will yield a product which has a similar spatial arrangement of the atoms rather than a very different one even if energetically favorable
    • Hine, J. Adv. Phys. Org. Chem. 1977, 15, 1-61. "A spontaneous reaction will yield a product which has a similar spatial arrangement of the atoms rather than a very different one even if energetically favorable."
    • (1977) Adv. Phys. Org. Chem , vol.15 , pp. 1-61
    • Hine, J.1
  • 63
    • 0004105856 scopus 로고
    • Longman Group Ltd, Harlow, U.K
    • Isaacs, N. Physical Organic Chemistry; Longman Group Ltd.: Harlow, U.K., 1995; pp 123-124.
    • (1995) Physical Organic Chemistry , pp. 123-124
    • Isaacs, N.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.