A new stereocontrolled, pyrylium-based route to conjugated dienynes: The first synthesis of Carduusyne A

Tetrahedron Letters

Volumn 37, Issue 11, 1996, Pages 1913-1916

  Charoenying, Patchanee ^a   Huw Davies, D ^b   McKerrecher, Darren ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARDUUSYNE A; POLYENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0029990258     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00153-0     Document Type: Article

References (27)

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3. For lead references see Negishi, E.; King, A. O.; Tour, J. M. Org. Synth., 1985, 64, 44; Nicolaou, K. C.; Zipkin, R. E.; Dolle, R. E.; Harris, B. D. J. Am. Chem. Soc., 1984, 106, 3548; Crousse, B.; Alami, A.; Linstrumelle, G. Tetrahedron Lett., 1995, 36, 4245.
4. For lead references see Negishi, E.; King, A. O.; Tour, J. M. Org. Synth., 1985, 64, 44; Nicolaou, K. C.; Zipkin, R. E.; Dolle, R. E.; Harris, B. D. J. Am. Chem. Soc., 1984, 106, 3548; Crousse, B.; Alami, A.; Linstrumelle, G. Tetrahedron Lett., 1995, 36, 4245.
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6. Furber, M.; Herbert, J. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. I, 1989, 683; Belosludtsev, Y. Y.; Borer, B. C.; Taylor, R. J. K. Synthesis, 1991, 320.
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11. Borer, B. C.; Taylor, R. J. K. J. Chem. Res.(S), 1990, 162; Faria De Medeiros, E.; Herbert, J. M.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. I, 1991, 2725; Borer, B. C.; Taylor, R. J. K. Synlett, 1992, 117; Hemming, K.; Taylor, R. J. K. J. Chem. Soc., Chem. Commun., 1993, 1409.
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18. 13C-NMR spectroscopy and by elemental analysis or high resolution mass spectrometry.
19. 3OD) 5.51 (1H, d, J 10.5Hz, H4), 6.09 (1H, dt, J 15.0, 7.5Hz, H7), 6.61 (1H, dd appears as t, J 10.5, 10.5Hz, H5), 6.79 (1H, dd, J 15.0, 10.5Hz, H6).
20. Shinoda, M.; Iseki, K.; Oguri, T.; Hayashi, Y.; Yamada, S.; Shibasaki, M. Tetrahedron Lett., 1986, 27, 87.
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26. 3) 78.6 (C1), 83.1 (C2), 107.4 (C3), 129.3 (C5), 139.0 (C6), 143.9 (C4).
27. 2 requires 371.2950 (2 ppm error).