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Volumn 71, Issue 3, 2006, Pages 1220-1225

Catalytic asymmetric total synthesis of (+)-lactacystin

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; GLUCOSE; MOLECULAR STRUCTURE; OPTIMIZATION; SYNTHESIS (CHEMICAL);

EID: 32144447583     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0524223     Document Type: Article
Times cited : (80)

References (61)
  • 42
    • 0034704642 scopus 로고    scopus 로고
    • For catalytic enantioselective Strecker reactions developed by other aroups, see: (a) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867-870.
    • (2000) Org. Lett. , vol.2 , pp. 867-870
    • Vachal, P.1    Jacobsen, E.N.2
  • 45
    • 7444246242 scopus 로고    scopus 로고
    • For recent examples of the synthesis of β-hydroxy carbonyl compounds using this method, see: (a) Trost, B. M.; Ball, Z. T. J. Am. Chem. Soc. 2004, 126, 13942-13944.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13942-13944
    • Trost, B.M.1    Ball, Z.T.2
  • 49
    • 32144451855 scopus 로고    scopus 로고
    • note
    • Compound 7 can be used as a masked α-hydroxy ketoimine equivalent. α-Hydroxy phosphinoylketoimines such as A or B were unstable, and we could not synthesize these compounds in a pure form. For the synthesis of 7, see Supporting Information for details. (Equation presented).
  • 53
    • 32144448667 scopus 로고    scopus 로고
    • note
    • 3, or HCN-EtOH) did not proceed well (<20% yield). The chiral Gd-8 complex generally produces significantly higher activity than that of strongly Lewis acidic achiral promoters.
  • 54
    • 32144454534 scopus 로고    scopus 로고
    • note
    • The use of HCN instead of 2,6-dimethylphenol did not improve the catalyst activity and enantioselectivity in this case.
  • 56
    • 32144436717 scopus 로고    scopus 로고
    • note
    • 13C NMR chemical shifts of 2 with the reported values.
  • 61
    • 32144454690 scopus 로고    scopus 로고
    • note
    • 2Si group could be introduced to 4 with excellent stereoselectivity and yield. The Tamao oxidation, however, did not proceed from this silylated product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.