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Volumn 43, Issue 33, 2004, Pages 4336-4338

Fully stereocontrolled total syntheses of (-)-cylindricine C and (-)-2-epicylindricine C: A departure in sulfonamide chemistry

Author keywords

Antitumor agents; Cyclization; Spiro compounds; Sulfonamides; Total synthesis

Indexed keywords

MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; PHENOLS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 4544303068     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460178     Document Type: Article
Times cited : (127)

References (44)
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    • total synthesis of (+)-cylindricines C, D, and E: b) B. M. Trost, M. T. Rudd, Org. Lett. 2003, 5, 4599;
    • (2003) Org. Lett. , vol.5 , pp. 4599
    • Trost, B.M.1    Rudd, M.T.2
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    • total synthesis of (±)-cylindricines A, D, and E: c) B. B. Snider, T. Liu, J. Org. Chem. 1997, 62, 5630;
    • (1997) J. Org. Chem. , vol.62 , pp. 5630
    • Snider, B.B.1    Liu, T.2
  • 12
    • 0034679048 scopus 로고    scopus 로고
    • For synthetic studies on the structurally related alkaloids, fasicularin and lepadiformine, see: a) H. Abe, S. Aoyagi, C. Kibayashi, J. Am. Chem. Soc. 2000, 122, 4583;
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 4583
    • Abe, H.1    Aoyagi, S.2    Kibayashi, C.3
  • 17
    • 0037118888 scopus 로고    scopus 로고
    • e) H. Abe, S. Aoyagi, C. Kibayashi, Angew. Chem. 2002, 114, 3143, Angew. Chem. Int. Ed. 2002, 41, 3017;
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3017
  • 22
    • 4544308702 scopus 로고    scopus 로고
    • note
    • Unpublished results from these laboratories; details will be provided in a forthcoming full paper.
  • 23
    • 4544356520 scopus 로고    scopus 로고
    • note
    • [3a]
  • 24
    • 4544333276 scopus 로고    scopus 로고
    • note
    • 2/MeOH;
  • 25
    • 4544332660 scopus 로고    scopus 로고
    • note
    • 2, 0 °C, (formation of the N,O-dimesyl derivative), 91% over two steps;
  • 26
    • 4544346683 scopus 로고    scopus 로고
    • note
    • 4/EtOH/THF, 94%;
  • 27
    • 4544222155 scopus 로고    scopus 로고
    • note
    • d) NaOH/dioxane, 80 °C, 90%. Ms = methanesulfonyl, TEA = triethylamine.
  • 28
    • 4544312982 scopus 로고    scopus 로고
    • note
    • Under identical conditions, cyclization of the corresponding methyl ether proceeded with d.r. = 3.5:1 and that of the TBDMS ether with d.r. = 4.5:1.
  • 29
    • 0003942864 scopus 로고
    • Wiley, New York
    • The structure of this material was confirmed by an X-ray crystallographic study of its desilylated analogue. The selectivity of the 1,4-addition of PhSH to 8 appears to be due to a Felkin-Anh-type stereoelectronic effect created by the strongly electro-negative sulfonamide nitrogen atom. For examples, see: a) E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, p. 875;
    • (1994) Stereochemistry of Organic Compounds , pp. 875
    • Eliel, E.L.1    Wilen, S.H.2
  • 37
    • 4544348292 scopus 로고    scopus 로고
    • note
    • 13C NMR (75 MHz) spectrometry.
  • 39
    • 0034724768 scopus 로고    scopus 로고
    • b) for an excellent bibliography on general directed organocuprate addition reactions,see: B. Breit, P. Demel, Tetrahedron 2000, 56, 2833.
    • (2000) Tetrahedron , vol.56 , pp. 2833
    • Breit, B.1    Demel, P.2
  • 40
    • 4544254526 scopus 로고    scopus 로고
    • note
    • For related processes, see reference [3g].
  • 42
    • 4544279165 scopus 로고    scopus 로고
    • note
    • [3e] (see Supporting Information).
  • 44
    • 4544243758 scopus 로고    scopus 로고
    • note
    • 2) for reference [3a].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.