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Volumn 51, Issue 41, 2010, Pages 5469-5472

Construction of a fully substituted cyclopentenone as the core skeleton of stemonamide via a Nazarov cyclization

Author keywords

C H amination; Natural product; Nazarov reaction; Stemona alkaloid; Synthetic study

Indexed keywords

ALKALOID DERIVATIVE; CYCLOPENTENONE; FERRIC CHLORIDE; KETONE DERIVATIVE; STEMONAMIDE; UNCLASSIFIED DRUG;

EID: 78649660867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.032     Document Type: Article
Times cited : (15)

References (30)
  • 10
    • 52949099149 scopus 로고    scopus 로고
    • For a review on torquoselective olefination, see: M. Shindo, and S. Mori Synlett 2008 2231
    • (2008) Synlett , pp. 2231
    • Shindo, M.1    Mori, S.2
  • 12
    • 0001563044 scopus 로고
    • For construction of α-exo-methylene cyclopentenones via Nazarov cyclization, see: M.A. Tius, and D.P. Astrab Tetrahedron Lett. 25 1984 1539
    • (1984) Tetrahedron Lett. , vol.25 , pp. 1539
    • Tius, M.A.1    Astrab, D.P.2
  • 15
    • 0030592823 scopus 로고    scopus 로고
    • For the total synthesis of natural products via cationic cyclopentannelation of allenyl ether, see: D.J. Drake, and M.A. Tius Tetrahedron Lett. 52 1996 14651
    • (1996) Tetrahedron Lett. , vol.52 , pp. 14651
    • Drake, D.J.1    Tius, M.A.2
  • 18
    • 77956530163 scopus 로고    scopus 로고
    • note
    • 3; DMF, room temperature (78% yield).
  • 19
    • 33751518128 scopus 로고    scopus 로고
    • For a review on ynolates, see: M. Shindo Tetrahedron 63 2007 10
    • (2007) Tetrahedron , vol.63 , pp. 10
    • Shindo, M.1
  • 22
    • 77956520673 scopus 로고    scopus 로고
    • note
    • 2, room temperature (57% yield).
  • 23
    • 77956553952 scopus 로고    scopus 로고
    • note
    • An ester having a methoxy group at the terminal position in place of TBDPSO gave the olefinated product in low yield. The reason for this is not clear.
  • 25
    • 77956556286 scopus 로고    scopus 로고
    • note
    • ++H): 339.2355, found: 339.2360.
  • 30
    • 77956498043 scopus 로고    scopus 로고
    • note
    • ++H): 294.1341, found: 294.1343.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.