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Volumn 12, Issue 22, 2010, Pages 5258-5261

(-)-lytophilippine a: Synthesis of a C1-C18 building block

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSE; LYTOPHILIPPINE A; MACROLIDE;

EID: 78449287251     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1023008     Document Type: Article
Times cited : (34)

References (59)
  • 9
    • 78449269001 scopus 로고    scopus 로고
    • Compound 4 has been prepared on 20 g scale in five steps from commercial 2-butyn-1-ol according to the published procedure; see
    • Compound 4 has been prepared on 20 g scale in five steps from commercial 2-butyn-1-ol according to the published procedure; see
  • 10
    • 64349087921 scopus 로고    scopus 로고
    • The synthesis requires access to preparative HPLC for the separation of vinyl ether double bond isomers
    • Rehbein, J.; Leick, S.; Hiersemann, M. J. Org. Chem. 2009, 74, 1531-1540 The synthesis requires access to preparative HPLC for the separation of vinyl ether double bond isomers.
    • (2009) J. Org. Chem. , vol.74 , pp. 1531-1540
    • Rehbein, J.1    Leick, S.2    Hiersemann, M.3
  • 12
    • 78449303283 scopus 로고    scopus 로고
    • For selected applications of the catalytic asymmetric Gosteli-Claisen rearrangement in natural product synthesis, see
    • For selected applications of the catalytic asymmetric Gosteli-Claisen rearrangement in natural product synthesis, see
  • 15
    • 33845282886 scopus 로고
    • Reduction in the presence of (R)- 7 provided (2 S)- 8 in 87% (dr = 93:7). Treatment with K-Selectride also delivered (2 S)- 8 (81%, dr = 85:15), albeit with limited scalability (1 g). Far inferior yields (60%) and diastereoselectivities (dr = 4:1) were obtained with (S)- 7
    • Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. Soc. 1987, 109, 5551-5553 Reduction in the presence of (R)- 7 provided (2 S)- 8 in 87% (dr = 93:7). Treatment with K-Selectride also delivered (2 S)- 8 (81%, dr = 85:15), albeit with limited scalability (1 g). Far inferior yields (60%) and diastereoselectivities (dr = 4:1) were obtained with (S)- 7
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5551-5553
    • Corey, E.J.1    Bakshi, R.K.2    Shibata, S.3
  • 29
    • 78449273058 scopus 로고    scopus 로고
    • Jäger, V. Synthesis 2000, 7, 1027-1033
    • (2000) Synthesis , vol.7 , pp. 1027-1033
    • Jäger, V.1
  • 33
    • 78449287388 scopus 로고    scopus 로고
    • Prepared in four steps from 11; see
    • Prepared in four steps from 11; see
  • 37
    • 0000786664 scopus 로고
    • Experimental details are provided in the Supporting Information
    • Gramatica, P.; Manitto, P.; Monti, D.; Speranza, G. Tetrahedron 1988, 44, 1299-1304 Experimental details are provided in the Supporting Information.
    • (1988) Tetrahedron , vol.44 , pp. 1299-1304
    • Gramatica, P.1    Manitto, P.2    Monti, D.3    Speranza, G.4
  • 52
    • 78449292273 scopus 로고    scopus 로고
    • The calculations were carried out with Gaussian03, see:.; Gaussian, Inc.: Wallingford, CT,. Full reference given in the Supporting Information
    • The calculations were carried out with Gaussian03, see: Frisch, M. J. Gaussian 03, revision E.01; Gaussian, Inc.: Wallingford, CT, 2004. Full reference given in the Supporting Information.
    • (2004) Gaussian 03, Revision E.01
    • Frisch, M.J.1
  • 53
    • 78449295865 scopus 로고    scopus 로고
    • Single-point self-consistent reaction field (SCRF) calculations using the PCM solvation model as implemented in Gaussian 03 (PCM, solvent = acetone) at the PCM//B3LYP/6-311++G(d,p) level support this notion and predict a free energy difference of 4.0 kcal/mol in favor of II
    • Single-point self-consistent reaction field (SCRF) calculations using the PCM solvation model as implemented in Gaussian 03 (PCM, solvent = acetone) at the PCM//B3LYP/6-311++G(d,p) level support this notion and predict a free energy difference of 4.0 kcal/mol in favor of II.
  • 56
    • 78449311148 scopus 로고    scopus 로고
    • 3 J coupling constant of the vinylic protons of 23 (16.1 Hz) is in good accordanced with reported value for the natural product (15.2 Hz)
    • 3 J coupling constant of the vinylic protons of 23 (16.1 Hz) is in good accordanced with reported value for the natural product (15.2 Hz).
  • 57
    • 78449299837 scopus 로고    scopus 로고
    • 4F in MeOH, see
    • 4F in MeOH, see
  • 59
    • 78449289335 scopus 로고    scopus 로고
    • 2OH, were not successful
    • 2OH, were not successful.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.