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Volumn 69, Issue 6, 2004, Pages 1837-1843

Palladium-Catalyzed Asymmetric Allylic Substitution of 2-Arylcyclohexenol Derivatives: Asymmetric Total Syntheses of (+)-Crinamine, (-)-Haemanthidine, and (+)-Pretazettine

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CATALYSIS; CRYSTALLIZATION; DERIVATIVES; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 1642343936     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030309b     Document Type: Article
Times cited : (53)

References (57)
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    • (a) Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1987; Vol. 30, p 251,
    • (1987) The Alkaloids , vol.30 , pp. 251
    • Martin, S.F.1
  • 2
    • 77956708370 scopus 로고    scopus 로고
    • Brossi, A., Ed.; Academic Press: New York
    • (b) Hoshino, O. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1998; Vol. 51, p 323.
    • (1998) The Alkaloids , vol.51 , pp. 323
    • Hoshino, O.1
  • 7
    • 1642318909 scopus 로고
    • Isolation of (-)-haemanthidine: (a) Boit, H. G. Chem. Ber. 1954, 87, 1339.
    • (1954) Chem. Ber. , vol.87 , pp. 1339
    • Boit, H.G.1
  • 9
    • 0016193388 scopus 로고
    • (b) Takagi, S.; Yamaki, M. Yakugaku Zasshi 1974, 94, 617; Chem. Abstr. 1974, 81, 74924y.
    • (1974) Chem. Abstr. , vol.81
  • 18
    • 0034719244 scopus 로고    scopus 로고
    • Total syntheses of (-)-haemanthidine, (+)-prettazetine, and (+)-tazettine: (k) Baldwin, S. W.; Debenham, J. S. Org. Lett, 2000, 2, 99.
    • (2000) Org. Lett. , vol.2 , pp. 99
    • Baldwin, S.W.1    Debenham, J.S.2
  • 25
    • 0043078708 scopus 로고
    • For the formal total synthesis of (±)-6a-epipretazettine (synthetic compound by Wildman) see: Wildman, W. C.; Bailey, D. T. J. Am. Chem. Soc. 1969, 91, 150).
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 150
    • Wildman, W.C.1    Bailey, D.T.2
  • 34
    • 0041154736 scopus 로고
    • Asymmetric total syntheses of crinine-type alkaloids: (a) [(+)-Maritidine] Yamada, S.-I.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1976, 57; Chem. Pharm. Bull. 1977, 25, 2681.
    • (1976) Tetrahedron Lett. , pp. 57
    • Yamada, S.-I.1    Tomioka, K.2    Koga, K.3
  • 35
    • 0017724269 scopus 로고
    • Asymmetric total syntheses of crinine-type alkaloids: (a) [(+)-Maritidine] Yamada, S.-I.; Tomioka, K.; Koga, K. Tetrahedron Lett. 1976, 57; Chem. Pharm. Bull. 1977, 25, 2681.
    • (1977) Chem. Pharm. Bull. , vol.25 , pp. 2681
  • 38
    • 0001731905 scopus 로고    scopus 로고
    • J. Org. Chem. 1998, 63, 3607.
    • (1998) J. Org. Chem. , vol.63 , pp. 3607
  • 43
    • 1642281371 scopus 로고    scopus 로고
    • note
    • The ee values of 13 and 14 were determined by HPLC analysis (DAICEL Chiralpak AD, hexane/2-propanol (9:1) and DAICEL CHIRAL-PAK AS, hexane/2-propanol (9:1), respectively).
  • 49
  • 55
    • 1642300870 scopus 로고    scopus 로고
    • note
    • 3g,h,4a-c a compound having the methyl group on nitrogen (in our case, the tosyl group) was treated under the same reaction conditions to give only an α-methoxylated product.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.