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Volumn 71, Issue 12, 2006, Pages 4549-4558

Practical, catalytic, asymmetric synthesis of β-lactones via a sequential ketene dimerization/hydrogenation process: Inhibitors of the thioesterase domain of fatty acid synthase

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACID SYNTHASE (FAS); KETENE FORMATION; LACTONES;

EID: 33744898777     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060392d     Document Type: Article
Times cited : (77)

References (66)
  • 5
    • 0001210617 scopus 로고    scopus 로고
    • For reviews describing asymmetric routes to β-lactones, see: (a) Yang, H. W.; Zhao, C.; Romo, D. Tetrahedron 1997, 53, 16471.
    • (1997) Tetrahedron , vol.53 , pp. 16471
    • Yang, H.W.1    Zhao, C.2    Romo, D.3
  • 14
    • 0037539910 scopus 로고    scopus 로고
    • (b) For a review on the use of ketenes in asymmetric synthesis, see: Orr, R. K.; Calter, M. A. Tetrahedron 2003, 59, 3545.
    • (2003) Tetrahedron , vol.59 , pp. 3545
    • Orr, R.K.1    Calter, M.A.2
  • 44
    • 33744898913 scopus 로고    scopus 로고
    • U.S. Patent 5525738
    • For a lead reference to processes for ketene dimerization, see: Zhang, J. J. U.S. Patent 5525738, 1996.
    • (1996)
    • Zhang, J.J.1
  • 46
    • 33744918617 scopus 로고    scopus 로고
    • Calter previously reported increased rates with silylated quinine derivatives, see ref 7a.
    • Calter previously reported increased rates with silylated quinine derivatives, see ref 7a.
  • 48
    • 33744935388 scopus 로고
    • U.S. Patent 2,763,664
    • For lead references to hydrogenation of diketene. see: (a) Sixt, J. U.S. Patent 2,763,664, 1956.
    • (1956)
    • Sixt, J.1
  • 52
    • 33744926535 scopus 로고    scopus 로고
    • note
    • Samples taken at 2, 4, 6, 12, and 18 h revealed no erosion of enantiomeric purity by chiral GC analysis for both ketene dimer 2a and cis-β-lactone 3a.
  • 56
    • 17044405496 scopus 로고    scopus 로고
    • For a review on the utility of β-lactones and their application as intermediates in natural product synthesis, see: Wang, Y.; Tennyson, R. L.; Romo, D. Heterocycles 2004, 64, 605.
    • (2004) Heterocycles , vol.64 , pp. 605
    • Wang, Y.1    Tennyson, R.L.2    Romo, D.3
  • 57
    • 33744932030 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.