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Volumn , Issue 9, 2004, Pages 1391-1398

Studies on the asymmetric dihydroxylation of advanced bryostatin C-ring segments

Author keywords

Asymmetric dihydroxylation; Bryostatin; Cinchona alkynes; Double stereoinduction; Quinidine based ligands

Indexed keywords

ALCOHOLS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 3042834234     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822400     Document Type: Article
Times cited : (10)

References (38)
  • 13
    • 0001216677 scopus 로고    scopus 로고
    • Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin
    • (a) Markó, I. E.; Svendsen, J. E. In Comprehensive Asymmetric Catalysis, Vol. II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 713-787.
    • (1999) Comprehensive Asymmetric Catalysis , vol.2 , pp. 713-787
    • Markó, I.E.1    Svendsen, J.E.2
  • 16
    • 3042781009 scopus 로고    scopus 로고
    • See also ref. 8b
    • (d) See also ref. 8b
  • 20
    • 3042824579 scopus 로고    scopus 로고
    • note
    • To determine the ratio of diastereoselectivity for the dihydroxylated lactol of 1 the diol was first transformed into the corresponding acetonide, followed by oxidation to lactone 11 (Equation 3). (Equation Presented)
  • 21
    • 3042703813 scopus 로고    scopus 로고
    • note
    • The synthesis of these fragments will be presented in due course.
  • 25
    • 3042741848 scopus 로고    scopus 로고
    • See also ref. 15
    • (c) See also ref. 15
  • 27
    • 0033531746 scopus 로고    scopus 로고
    • For synthetic applications of dihydroxylation reactions of terminal double bonds using the AQN-ligand see: (a) Denmark, S. E.; Martinsborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046. (b) Burke, S. D.; Jiang, L. Org. Lett. 2001, 3, 1953. (c) See also ref. 13.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3046
    • Denmark, S.E.1    Martinsborough, E.A.2
  • 28
    • 0035859355 scopus 로고    scopus 로고
    • For synthetic applications of dihydroxylation reactions of terminal double bonds using the AQN-ligand see: (a) Denmark, S. E.; Martinsborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046. (b) Burke, S. D.; Jiang, L. Org. Lett. 2001, 3, 1953. (c) See also ref. 13.
    • (2001) Org. Lett. , vol.3 , pp. 1953
    • Burke, S.D.1    Jiang, L.2
  • 29
    • 0033531746 scopus 로고    scopus 로고
    • See also ref. 13
    • For synthetic applications of dihydroxylation reactions of terminal double bonds using the AQN-ligand see: (a) Denmark, S. E.; Martinsborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046. (b) Burke, S. D.; Jiang, L. Org. Lett. 2001, 3, 1953. (c) See also ref. 13.
  • 38
    • 3042737371 scopus 로고    scopus 로고
    • note
    • Although complete conversion was noted in these experiments, the yield of isolated product was generally low when structurally complex substrates were converted. Thus far, no degradation products could be isolated, implying the formation of highly water-soluble side-products.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.