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Volumn 62, Issue 14, 2006, Pages 3329-3343

Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues

Author keywords

12 PGJ2; 15 Deoxy 12,14 PGJ2; Aldol reaction; Cyclopentenone; Palladium; PPAR

Indexed keywords

PALLADIUM; PROSTAGLANDIN DERIVATIVE;

EID: 33644893966     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.01.051     Document Type: Article
Times cited : (46)

References (57)
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  • 23
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    • note
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    • note
    • β-Hydride elimination is probably the reason, though we did not obtain any evidence for the production of 3-cyclopentenon.
  • 40
    • 33644914925 scopus 로고    scopus 로고
    • note
    • 13C NMR spectroscopy (δ 126.3 and 133.4), which is probably responsible for the trans olefin isomer.
  • 44
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    • note
    • 25
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    • note
    • 3 in the transition state (B ) assisted the syn elimination effectively.
  • 52
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    • note
    • Deprotection of the TBS group with TBAF in THF and with NBS in wet DMSO was unsuccessful.
  • 53
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    • note
    • The stereochemistry of the newly formed olefin at C(13) was assigned by the chemical shift of the C(13)-H: (E)-isomer 31, δ 6.87 (d, J=11 Hz); (Z)-isomer 34, δ 6.43 (d, J=11 Hz).
  • 54
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    • The corresponding alcohol is synthesized in racemic form with low product selectivity in low yield: H. Mayr, and B. Grubmüller Angew. Chem., Int. Ed. Engl. 17 1978 130 131
    • (1978) Angew. Chem., Int. Ed. Engl. , vol.17 , pp. 130-131
    • Mayr, H.1    Grubmüller, B.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.