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Volumn 125, Issue 32, 2003, Pages 9801-9807

A novel and general synthetic pathway to strychnos indole alkaloids: Total syntheses of (-)-tubifoline, (-)-dehydrotubifoline, and (-)-strychnine using palladium-catalyzed asymmetric allylic substitution

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHETIC PATHWAYS;

EID: 0042626234     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029382u     Document Type: Article
Times cited : (120)

References (57)
  • 4
    • 0034669655 scopus 로고    scopus 로고
    • Recently, similar type reactions were reported by two groups: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 11262. (b) Hamada, Y.; Sakaguchi, K.; Hatano, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11262
    • Trost, B.M.1    Toste, F.D.2
  • 5
    • 0035847526 scopus 로고    scopus 로고
    • Recently, similar type reactions were reported by two groups: (a) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 11262. (b) Hamada, Y.; Sakaguchi, K.; Hatano, K.; Hara, O. Tetrahedron Lett. 2001, 42, 1297.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 1297
    • Hamada, Y.1    Sakaguchi, K.2    Hatano, K.3    Hara, O.4
  • 8
    • 0041641638 scopus 로고    scopus 로고
    • note
    • iPrOH = 9:1).
  • 9
    • 0042142607 scopus 로고    scopus 로고
    • note
    • The ee's of 5d and 5e were determined after conversion into 5c.
  • 11
    • 0001279801 scopus 로고
    • Palladium-catalyzed allylation using allyl vinyl carbonate was reported. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1793
    • Tsuji, J.1    Minami, I.2    Shimizu, I.3
  • 12
    • 0013553595 scopus 로고
    • Palladium-catalyzed allylation using allyl vinyl carbonate was reported. (b) Tsuji, J.; Minami, I.; Shimizu, I. Tetrahedron Lett. 1983, 24, 1793. (c) Shimizu, I.; Minami, I.; Tsuji, J. Tetrahedron Lett. 1983, 24, 1797.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 1797
    • Shimizu, I.1    Minami, I.2    Tsuji, J.3
  • 13
    • 0042142601 scopus 로고    scopus 로고
    • note
    • iPrOH = 9:1) after desilylation by treatment with 4 N HCl, respectively.
  • 36
    • 0042643525 scopus 로고    scopus 로고
    • note
    • D -311̊ (c 0.236, AcOEt).
  • 46
    • 0034273688 scopus 로고    scopus 로고
    • For a review of the total synthesis of strychnine, see: Bonjoch, J.; Solé, D. Chem. Rev. 2000, 100, 3455.
    • (2000) Chem. Rev. , vol.100 , pp. 3455
    • Bonjoch, J.1    Solé, D.2
  • 52
    • 0037009048 scopus 로고    scopus 로고
    • (f) Very recently, Bodwell reported the total synthesis of (±)-strychnine: Bodwell, G. J.; Li, J. Angew. Chem., Int. Ed. 2002, 41, 3261.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3261
    • Bodwell, G.J.1    Li, J.2
  • 56
    • 0042643523 scopus 로고    scopus 로고
    • note
    • iPrOH 95/5).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.