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Volumn , Issue 4, 1999, Pages 325-326

A formal synthesis of (+)-pyripyropene A using a biomimetic epoxy-olefin cyclisation

Author keywords

[No Author keywords available]

Indexed keywords

(+) PYRIPYROPENE; ALKENE; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; GERANIOL; UNCLASSIFIED DRUG;

EID: 0033590662     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808644c     Document Type: Article
Times cited : (20)

References (32)
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    • β-Keto esters are known to cyclise through oxygen rather than carbon, see: T. R. Hoye, A. J. Caruso and M. J. Kurth, J. Org. Chem., 1981, 46, 3550; J. D. White, R. W. Skeean and G. L. Trammell, J. Org. Chem., 1985, 50, 1939.
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    • note
    • Tanis showed that the benzyl ether of the epoxy alcohol was superior to silyl protected analogues: See ref. 7.
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    • For successful examples of (epoxy alcohol)-olefin cyclisations, see: T. Frejd, L. Pettersson and G. Magnusson, Tetrahedron Lett., 1987, 28, 2753; M. E. Jung, Y. M. Cho and Y. H. Jung, Tetrahedron Lett., 1996, 37, 3; G. Stork, T. Doi and L. Liu, Tetrahedron Lett., 1997, 38, 7471. In each case, the system was set up to prepare monocycles only.
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    • 0030025329 scopus 로고    scopus 로고
    • For successful examples of (epoxy alcohol)-olefin cyclisations, see: T. Frejd, L. Pettersson and G. Magnusson, Tetrahedron Lett., 1987, 28, 2753; M. E. Jung, Y. M. Cho and Y. H. Jung, Tetrahedron Lett., 1996, 37, 3; G. Stork, T. Doi and L. Liu, Tetrahedron Lett., 1997, 38, 7471. In each case, the system was set up to prepare monocycles only.
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    • Jung, M.E.1    Cho, Y.M.2    Jung, Y.H.3
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    • For successful examples of (epoxy alcohol)-olefin cyclisations, see: T. Frejd, L. Pettersson and G. Magnusson, Tetrahedron Lett., 1987, 28, 2753; M. E. Jung, Y. M. Cho and Y. H. Jung, Tetrahedron Lett., 1996, 37, 3; G. Stork, T. Doi and L. Liu, Tetrahedron Lett., 1997, 38, 7471. In each case, the system was set up to prepare monocycles only.
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    • note
    • From molecular modelling it was found that 22 was lower in energy than the conjugated tetrasubstituted double bond isomer.
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    • note
    • The optimised procedure required refluxing 11 with NaH (5 equiv.) in THF for 4 h followed by addition of BnBr and refluxing for a further 2 h. Less isomerisation was observed if 11 was refluxed with NaH for a shorter time.
  • 32
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    • note
    • 13C NMR, mass and IR analyses.


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