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Volumn 41, Issue 5, 2000, Pages 587-590

Total synthesis of (-)-eburnamonine and (+)-epi-eburnamonine from a chiral non-racemic 4,4-disubstituted γ-lactone

Author keywords

Asymmetric synthesis; Insertion; Rhodium(II) carbenoid; Tertiary C H

Indexed keywords

GAMMA LACTONE DERIVATIVE; VINBURNINE;

EID: 0034728123     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02131-0     Document Type: Article
Times cited : (26)

References (28)
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    • (b) Fuji, K. Chem. Rev. 1993, 93, 2037.
    • (1993) Chem. Rev. , vol.93 , pp. 2037
    • Fuji, K.1
  • 11
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    • For enantioselective synthesis, see: Compound 1a: (a)
    • For enantioselective synthesis, see: Compound 1a: (a) Schultz, A. G.; Pettus, L. J. Org. Chem. 1997, 62, 6855.
    • (1997) J. Org. Chem. , vol.62 , pp. 6855
    • Schultz, A.G.1    Pettus, L.2
  • 18
    • 0001597804 scopus 로고
    • (a) Attempted reduction of allylated 6 with LAH gave products that had resulted from reduction of the oxazolidinone moiety. (b) All new compounds showed satisfactory NMR, elemental and HRMS analyses
    • (a) Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141. Attempted reduction of allylated 6 with LAH gave products that had resulted from reduction of the oxazolidinone moiety. (b) All new compounds showed satisfactory NMR, elemental and HRMS analyses.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 6141
    • Evans, D.A.1    Britton, T.C.2    Ellman, J.A.3
  • 21
    • 0000932229 scopus 로고
    • Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196. For a related copper-carbenoid mediated process, see: Ledon, H.; Linstrumelle, G.; Julia, S. Tetrahedron Lett. 1973, 25.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 196
    • Taber, D.F.1    Petty, E.H.2    Raman, K.3
  • 22
    • 49549169780 scopus 로고
    • For a related copper-carbenoid mediated process, see
    • Taber, D. F.; Petty, E. H.; Raman, K. J. Am. Chem. Soc. 1985, 107, 196. For a related copper-carbenoid mediated process, see: Ledon, H.; Linstrumelle, G.; Julia, S. Tetrahedron Lett. 1973, 25.
    • (1973) Tetrahedron Lett. , pp. 25
    • Ledon, H.1    Linstrumelle, G.2    Julia, S.3
  • 25
    • 0343658289 scopus 로고    scopus 로고
    • 2, 35-40°C, 10 h) led to a 1:4 ratio of 15a:15b
    • 2, 35-40°C, 10 h) led to a 1:4 ratio of 15a:15b.
  • 26
    • 0343658290 scopus 로고    scopus 로고
    • 3b 107-108.5°C
    • 3b 107-108.5°C.
  • 28
    • 0343222675 scopus 로고    scopus 로고
    • 3f 145-146°C
    • 3f 145-146°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.