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Volumn 12, Issue 1, 2010, Pages 36-39

Stereocontrolled synthesis of C1-C17 fragment of narasin via a free radical-based approach

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL; NARASIN; PYRAN DERIVATIVE;

EID: 73949112664     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902414u     Document Type: Article
Times cited : (17)

References (30)
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    • Veterinary applications
    • Westley, J. W. , Ed.; M. Dekker: New York, Basel
    • Ruff, M. D. Veterinary Applications. In Polyether Antibiotics; Westley, J. W. , Ed.; M. Dekker: New York, Basel, 1982.
    • (1982) Polyether Antibiotics
    • Ruff, M.D.1
  • 3
    • 0001006715 scopus 로고
    • Total synthesis of narasin and salinomycin
    • Laidler, K. J., Ed.; Pergamon: Oxford
    • (a) Kishi, Y.; Hatakeyama, S. Lewis, M. D. Total Synthesis of Narasin and Salinomycin. In Frontiers of Chemistry; Laidler, K. J., Ed.; Pergamon: Oxford, 1982.
    • (1982) Frontiers of Chemistry
    • Kishi, Y.1    Hatakeyama, S.2    Lewis, M.D.3
  • 5
    • 0024320645 scopus 로고
    • There has been considerable effort toward the synthesis of salinomycin
    • There has been considerable effort toward the synthesis of salinomycin: (a) Horita, K.; Nagato, S.; Oikawa, O.; Yonemitsu, O. Chem. Pharm. Bull. 1989, 37, 1726.
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 1726
    • Horita, K.1    Nagato, S.2    Oikawa, O.3    Yonemitsu, O.4
  • 15
    • 0033717307 scopus 로고    scopus 로고
    • For a review on polyether ionophores, see: Faul, M. M.; Huff, B. E. Chem. Rev. 2000, 100, 2407.
    • (2000) Chem. Rev. , vol.100 , pp. 2407
    • Faul, M.M.1    Huff, B.E.2
  • 19
    • 73949143718 scopus 로고    scopus 로고
    • In previous works towards the synthesis of narasin and salinomycin, the C9-C10 bond was generated by an anti aldol reaction with moderate stereoselectivities. See ref 4.
    • In previous works towards the synthesis of narasin and salinomycin, the C9-C10 bond was generated by an anti aldol reaction with moderate stereoselectivities. See ref 4.
  • 23
    • 73949088568 scopus 로고    scopus 로고
    • At this stage, the presence of amide rotamers complicated the determination of the diastereoselectivity of the newly formed stereocenter. The dr was determined after cleavage of the pseudoephedrine moiety.
    • At this stage, the presence of amide rotamers complicated the determination of the diastereoselectivity of the newly formed stereocenter. The dr was determined after cleavage of the pseudoephedrine moiety.
  • 26
    • 73949109347 scopus 로고    scopus 로고
    • Only the conformers of the chair-like T.S. are considered as the kinetically controlled reaction should not favor the attack that proceeds through the boat-like T.S.
    • Only the conformers of the chair-like T.S. are considered as the kinetically controlled reaction should not favor the attack that proceeds through the boat-like T.S.
  • 28
    • 70350714361 scopus 로고    scopus 로고
    • For recent studies related to nucleophilic substitutions of tetrahydropyran acetals, see: Krumper, J. R.; Salamant, W. A.; Woerpel, K. A. J. Org. Chem. 2009, 74, 8039, and references therein.
    • (2009) J. Org. Chem. , vol.74 , pp. 8039
    • Krumper, J.R.1    Salamant, W.A.2    Woerpel, K.A.3
  • 29
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    • See Supporting Information for details that provide proof of stereochemical assignments.
    • See Supporting Information for details that provide proof of stereochemical assignments.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.