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Volumn 44, Issue 22, 2005, Pages 3481-3484

Total synthesis of 2-(5,6-epoxyisoprostane A2)phosphorylcholine and elucidation of the relative configuration of the isoprostane moiety

Author keywords

Aldol reaction; Isoprostanes; Phospholipids; Phosphorylcholine; Total synthesis

Indexed keywords

ACETONE; ALDEHYDES; CONDENSATION; LIPIDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 20444395864     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500534     Document Type: Article
Times cited : (35)

References (49)
  • 9
    • 0037243077 scopus 로고    scopus 로고
    • M. E. Jung, A. Kers, G. Subbanagounder, J. A. Berliner, Chem. Commun. 2003, 196-197. It is uncertain that the 1,4-addition of the cis-2-heptenyl anion to enone 5 would proceed at the terminal carbon atom of the anion regioselectively with retention of the cis olefin geometry.
    • (2003) Chem. Commun. , pp. 196-197
    • Jung, M.E.1    Kers, A.2    Subbanagounder, G.3    Berliner, J.A.4
  • 27
    • 20444366367 scopus 로고    scopus 로고
    • note
    • 3-assisted elimination generally produces the thermodynamically stable alkene (see reference [10] and the references cited therein).
  • 31
    • 20444379087 scopus 로고    scopus 로고
    • note
    • 3.
  • 32
    • 20444377459 scopus 로고    scopus 로고
    • note
    • 3 set at δ = 7.24 instead of 7.26 ppm).
  • 33
    • 20444417962 scopus 로고    scopus 로고
    • note
    • 3) and subsequent lactonization of the resulting diol. (Chemical Equation Presented)
  • 43
    • 20444392534 scopus 로고    scopus 로고
    • note
    • 2 to afford the product in 77% yield.
  • 46
    • 0035832085 scopus 로고    scopus 로고
    • We have used the Yamaguchi reagent for the macrocyclization of macrosphelides C, F, G, and H: a) Y. Kobayashi, H. P. Acharya, Tetrahedron Lett. 2001, 42, 2817-2820;
    • (2001) Tetrahedron Lett. , vol.42 , pp. 2817-2820
    • Kobayashi, Y.1    Acharya, H.P.2
  • 48
    • 20444427019 scopus 로고    scopus 로고
    • note
    • Because of the low solubility of the lyso-PC, toluene, the standard solvent for the Yamaguchi reaction, was not used.
  • 49
    • 20444383319 scopus 로고    scopus 로고
    • note
    • Prepared from racemic glycidol according to a literature method; see reference [19b].


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.