Control of stereochemistry in an intramolecular Diels-Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 23, 1997, Pages 3531-3536

  Bush, Edward J ^a,b   Jones, David W ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748607731     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a702761c     Document Type: Article

References (12)

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2. D. Craig, D. A. Fischer, O. Kemal, A. Marsh, T. Plessner, A. M. Z. Slawin and D. J. Williams, Tetrahedron, 1991, 47, 3095.
3. S. Niwayama and K. N. Houk, Tetrahedron Lett., 1993, 34, 1251;
4. E. Piers and K. A. Ellis, Tetrahedron Lett., ibid., 1993, 34, 1875 and references cited by these authors.
5. 2Et generally prefers outward conrotation in competition with hydrogen (but compare K. Shishido, E. Shitara, K. Fukumoto and T. Kametani, J. Am. Chem. Soc., 1985, 107, 5810;
6. C. W. Jefford, G. Bernardinelli, Y. Wang, A. B. Spellmeyer and K. N. Houk, J. Am. Chem. Soc., 1992, 114, 1157).
7. T. Kametani, M. Tsubuki, Y. Shiratori, Y. Kato, H. Nemoto, M. Ihara, K. Fukumoto and F. Satoh, J. Org. Chem., 1977, 42, 2672.
8. C. W. G. Fishwick and D. W. Jones, ortho-Quinonoid Compounds in The Chemistry of Quinonoid Compounds, ed. S. Patai and Z. Rappoport, Wiley, 1988, vol. II, pp. 403-453 and cited references.
9. Preliminary communication of some of these results: E. J. Bush, D. W. Jones and M. Thornton-Pett, Tetrahedron Lett., 1994, 35, 9755.
10. E. J. Bush, D. W. Jones and F. M. Nongrum, J. Chem. Soc., Chem. Commun., 1994, 2145.
11. B. J. Hunt and W. Rigby, Chem. Ind. (London), 1967, 1868.
12. D. D. Perrin, W. C. F. Armagego and D. Perrin, The Purification of Laboratory Chemicals, Pergamon, Oxford, 2nd edn., 1980.