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Volumn 69, Issue 24, 2004, Pages 8429-8436

Design of a nonreductive method for chemoselective cleavage of hydrazines in the presence of unsaturations: Application to a stereoconvergent three-component synthesis of (-)-methyl palustramate

Author keywords

[No Author keywords available]

Indexed keywords

FUNCTIONS; MATHEMATICAL TRANSFORMATIONS; OLEFINS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 9344249052     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048581o     Document Type: Article
Times cited : (43)

References (68)
  • 6
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    • For recent examples of applications of multicomponent reactions in target-oriented synthesis, see: (a) Trost, B. M.; Higuchi, R. I. J. Am. Chem. Soc. 1996, 118, 10094-10105.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 10094-10105
    • Trost, B.M.1    Higuchi, R.I.2
  • 23
    • 1542612350 scopus 로고
    • For early isolation and structural elucidation through synthetic and degradation studies (note that the originally postulated C4-C5 dehydro structure of palustrine was wrong, and was later corrected to C3-C4 dehydro on the basis of refs 10a-c), see: (a) Karrer, P.; Eugster, C. H. Helv. Chim. Acta 1948, 31, 1062-1066.
    • (1948) Helv. Chim. Acta , vol.31 , pp. 1062-1066
    • Karrer, P.1    Eugster, C.H.2
  • 31
    • 0001979972 scopus 로고
    • The chemistry of the cinchona alkaloids
    • Manske, R. H. F., Ed.; Academic Press: New York, Chapter 16
    • Turner, R. B.; Woodward, R. B. The Chemistry of the Cinchona Alkaloids. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1953; Vol. 3, Chapter 16.
    • (1953) The Alkaloids , vol.3
    • Turner, R.B.1    Woodward, R.B.2
  • 32
    • 85008131150 scopus 로고
    • Syntheses of members of the palustrine family: Racemic syntheses of the wrong structure of palustrine: (a) Natsume, M.; Ogawa, M.; Yoda, I.; Shiro, M. Chem. Pharm. Bull. 1984, 32, 812-814.
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 812-814
    • Natsume, M.1    Ogawa, M.2    Yoda, I.3    Shiro, M.4
  • 34
    • 85008272034 scopus 로고
    • Synthesis of racemic palustrine and structure revision: (c) Natsume, M.; Ogawa, M. Chem. Pharm. Bull. 1984, 32, 3789-3791.
    • (1984) Chem. Pharm. Bull. , vol.32 , pp. 3789-3791
    • Natsume, M.1    Ogawa, M.2
  • 37
    • 0032538579 scopus 로고    scopus 로고
    • Total synthesis of (-)-methyl palustramate: (f) Angle, S. R.; Henry, R. M. J. Org. Chem. 1998, 63, 7490-7497.
    • (1998) J. Org. Chem. , vol.63 , pp. 7490-7497
    • Angle, S.R.1    Henry, R.M.2
  • 38
    • 0034704647 scopus 로고    scopus 로고
    • For a recent asymmetric synthesis of cannabisativine see: (g) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855-857.
    • (2000) Org. Lett. , vol.2 , pp. 855-857
    • Kuethe, J.T.1    Comins, D.L.2
  • 53
    • 4544229370 scopus 로고
    • Selected references: (a) Wucherpfennig, W. Tetrahedron Lett. 1967, 3235. Wucherpfennig, W. Ann. Chem. 1971, 761, 16-27.
    • (1967) Tetrahedron Lett. , pp. 3235
    • Wucherpfennig, W.1
  • 54
    • 84943112872 scopus 로고
    • Selected references: (a) Wucherpfennig, W. Tetrahedron Lett. 1967, 3235. Wucherpfennig, W. Ann. Chem. 1971, 761, 16-27.
    • (1971) Ann. Chem. , vol.761 , pp. 16-27
    • Wucherpfennig, W.1
  • 59
    • 0000054463 scopus 로고
    • and references therein
    • For example, N-acylated cis-2,6-disubstituted piperidines exist in the "diaxial" conformation to escape A1,3 strain between the planar exocyclic amide group and the neighboring substituents in the "diequatorial" conformation: Natsume, M.; Ogawa, M. Chem. Pharm. Bull. 1982, 30, 3442-3445 and references therein. In the case of compounds 11, the planar hydrazine can be considered isosteric to an acyl group.
    • (1982) Chem. Pharm. Bull. , vol.30 , pp. 3442-3445
    • Natsume, M.1    Ogawa, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.