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Volumn 69, Issue 26, 2004, Pages 9109-9122

Total synthesis of the Kopsia lapidilecta alkaloid (±)-lapidilectine B

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AROMATIC COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 10844276455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048917u     Document Type: Article
Times cited : (107)

References (68)
  • 1
    • 0000438881 scopus 로고
    • (a) Margraf, F. Blumea 1972, 20, 416-425.
    • (1972) Blumea , vol.20 , pp. 416-425
    • Margraf, F.1
  • 26
    • 0036694457 scopus 로고    scopus 로고
    • For reviews of alkaloid synthesis with 2-azaallyllithiums see ref 8c and: Pearson, W. H. Pure Appl. Chem. 2002, 74, 1339-1347.
    • (2002) Pure Appl. Chem. , vol.74 , pp. 1339-1347
    • Pearson, W.H.1
  • 30
    • 0000705335 scopus 로고
    • For the most relevant example of such an aminocarbonylation strategy, see: (a) Tamaru, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5731-5741.
    • (1988) J. Org. Chem. , vol.53 , pp. 5731-5741
    • Tamaru, Y.1    Hojo, M.2    Yoshida, Z.3
  • 32
    • 85081434160 scopus 로고    scopus 로고
    • note
    • See the Supporting Information.
  • 47
    • 0033766956 scopus 로고    scopus 로고
    • For recent examples of oxidation of cyclic hemiacetals to γ-lactones with Fétizon's reagent, see: (a) Tatsuta, K.; Takahashi, M.; Tanaka, N.; Chikauchi, K. J. Antibiot. 2000, 53, 1231-1234.
    • (2000) J. Antibiot. , vol.53 , pp. 1231-1234
    • Tatsuta, K.1    Takahashi, M.2    Tanaka, N.3    Chikauchi, K.4
  • 49
    • 0141516298 scopus 로고    scopus 로고
    • For recent examples of oxidation of cyclic hemiacetals to γ-lactones with PCC, see: (a) Clayden, J.; Kenworthy, M. N.; Helliwell, M. Org. Lett. 2003, 5, 831-834.
    • (2003) Org. Lett. , vol.5 , pp. 831-834
    • Clayden, J.1    Kenworthy, M.N.2    Helliwell, M.3
  • 60
    • 0007590568 scopus 로고
    • Sulfoxides and selenoxides are known to prefer thermal elimination away from heteroatoms, see ref 8b and: (a) Sharpless, K. B.; Lauer, E. F. J. Am. Chem. Soc. 1973, 95, 2697.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 2697
    • Sharpless, K.B.1    Lauer, E.F.2
  • 62
    • 85081439349 scopus 로고    scopus 로고
    • note
    • In our initial communication (ref 10), we reported in error that 50 was isolated as an inseparable mixture of two diastereomers, which we have presently shown to be carbamate rotamers. See the Supporting Information.
  • 68
    • 85081440198 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy, see ref 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.