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Volumn 127, Issue 29, 2005, Pages 10186-10187

Sequential catalytic asymmetric Heck-iminium ion cyclization: Enantioselective total synthesis of the Strychnos alkaloid minfiensine

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4 TETRAHYDRO 9A,4A BIS(IMINOETHANO) 9H CARBAZOLE; 3,4 DIHYDRO 9A,4A BIS(IMINOETHANO) 9H CARBAZOLE; ALKALOID DERIVATIVE; ECHITAMINE; IMINE; MINFIENSINE; PLANT EXTRACT; STRYCHNOS EXTRACT; UNCLASSIFIED DRUG; VINCORINE;

EID: 22944450392     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0533895     Document Type: Article
Times cited : (145)

References (29)
  • 5
    • 33444462005 scopus 로고    scopus 로고
    • note
    • 2.4
  • 6
    • 1842851813 scopus 로고    scopus 로고
    • Catalytic asymmetric Heck cyclizations have been proven to have wide utility for constructing quaternary carbon stereocenters of natural products. See: (a) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363-5367.
    • (2004) Proc. Natl. Acad. Sci. U.S.A. , vol.101 , pp. 5363-5367
    • Douglas, C.J.1    Overman, L.E.2
  • 15
    • 33444462124 scopus 로고    scopus 로고
    • note
    • The use of BINAP as the ligand resulted in extensive double bond migration to form the fully conjugated dienyl carbamate.
  • 18
    • 33444458298 scopus 로고    scopus 로고
    • note
    • Intermediate 11 can be isolated and converted to 12 in a separate step; the overall yield in this case was 74%.
  • 19
    • 33444454667 scopus 로고    scopus 로고
    • note
    • Absolute configuration was secured by single-crystal X-ray analysis of a heavy atom derivative.
  • 20
    • 33444455182 scopus 로고    scopus 로고
    • note
    • The β-epoxide is isolated in 10% yield.
  • 22
    • 33444474725 scopus 로고    scopus 로고
    • note
    • Attempted acidic cleavage of the Boc protecting group at the allylic alcohol stage led to fragmentation of the six-membered ring.
  • 26
    • 0030598098 scopus 로고    scopus 로고
    • (b) Jeffery, T. Tetrahedron 1996, 52, 10113-10130.
    • (1996) Tetrahedron , vol.52 , pp. 10113-10130
    • Jeffery, T.1
  • 27
    • 33444471341 scopus 로고    scopus 로고
    • note
    • Attempts to directly introduce the methyl ester by carbonylative trapping of the alkylpalladium intermediate generated from Heck cyclization of 17 have proven unsuccessful thus far.
  • 29
    • 33444460481 scopus 로고    scopus 로고
    • note
    • 8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.