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Volumn 8, Issue 18, 2006, Pages 4007-4010

The enantioselective Birch-Cope sequence for the synthesis of carbocyclic quaternary stereocenters. Application to the synthesis of (+)-mesembrine

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EID: 33748922075     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0615228     Document Type: Article
Times cited : (39)

References (44)
  • 4
    • 33746877740 scopus 로고    scopus 로고
    • Christoffers, J., Baro, A., Eds.; Wiley-VCH: Weinheim, Federal Republic of Germany
    • For reviews see: (d) Quaternary Stereocenters; Christoffers, J., Baro, A., Eds.; Wiley-VCH: Weinheim, Federal Republic of Germany, 2005.
    • (2005) Quaternary Stereocenters
  • 9
    • 0001521888 scopus 로고
    • (i) Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 13
    • 0033591925 scopus 로고    scopus 로고
    • For reviews of the asymmetric Birch reduction-alkylation, see: (b) Schultz, A. G. Chem. Commun. 1999, 1263-1271.
    • (1999) Chem. Commun. , pp. 1263-1271
    • Schultz, A.G.1
  • 17
    • 24944509594 scopus 로고    scopus 로고
    • For leading references to previous enantioselective syntheses of (-)-mesembrine, see: (a) Taber, D. F.; He, Y. J. Org. Chem. 2005, 70, 7711-7714.
    • (2005) J. Org. Chem. , vol.70 , pp. 7711-7714
    • Taber, D.F.1    He, Y.2
  • 30
    • 33748945610 scopus 로고    scopus 로고
    • PCT Int. Appl., WO 9746234 CAN 128:80030, 1997
    • Gericke, N. P.; VanWyk, B.-E. PCT Int. Appl., WO 9746234 CAN 128:80030, 1997.
    • Gericke, N.P.1    VanWyk, B.-E.2
  • 31
    • 33748922491 scopus 로고    scopus 로고
    • note
    • A diastereomeric mixture of 4 was synthesized as described in ref 3a. A diastereomeric mixture of 8 was generated by modifying the Birch reduction conditions, i.e., removal of NHs, as described in ref 3a.
  • 32
    • 33748928857 scopus 로고    scopus 로고
    • note
    • γ-Alkylation of amide enolates derived from Birch reduction has previously been reported, see ref 3a and references therein.
  • 34
    • 0038695134 scopus 로고    scopus 로고
    • For reviews of the Cope rearrangement, see: (b) Nubbemeyer, U. Synthesis 2003, 7, 961-1008.
    • (2003) Synthesis , vol.7 , pp. 961-1008
    • Nubbemeyer, U.1
  • 35
    • 0000746177 scopus 로고
    • Cope, oxy-cope and anionic oxy-cope rearrangements
    • Trost, B. M., Fleming, I., Eds., Pergamon Press: Oxford, UK, Chapter 7.1
    • (c) Hill, R. K. Cope, Oxy-Cope and Anionic Oxy-Cope Rearrangements. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds., Pergamon Press: Oxford, UK, 1991; Vol. 5, Chapter 7.1.
    • (1991) Comprehensive Organic Synthesis , vol.5
    • Hill, R.K.1
  • 38
    • 0345761344 scopus 로고    scopus 로고
    • For other examples of chemoselective biaryl Birch reduction-alkylations, see ref 11 and: (a) Guo, Z.; Schultz, A. G. Tetrahedron Lett. 2004, 45, 919-921.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 919-921
    • Guo, Z.1    Schultz, A.G.2
  • 44
    • 18744369985 scopus 로고
    • Molybdenum hexacarbonyl deallylation and decarboxylation of a β-ketoester has been described: Tsuji, J.; Minami, I.; Shimizu, I. Chem. Lett. 1984, 10, 1721-1724.
    • (1984) Chem. Lett. , vol.10 , pp. 1721-1724
    • Tsuji, J.1    Minami, I.2    Shimizu, I.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.