Displacement of bridgehead sulfonate esters with organometallic reagents: Synthesis of 13-alkylated gibberellins

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1997, Pages 2989-2995

  Penny, Martin ^a   Westaway, Susan M ^a   Willis, Christine L ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748657827     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703587j     Document Type: Article

References (35)

1. T. J. Ingram, J. B. Reid, I. C Murfet, P. Gaskin, C. L. Willis and J. MacMillan, Planta, 1984, 160, 455.
2. C. R. Spray, B. O. Phinney, S. J. Gilmour and J. MacMillan, Planta, 1984, 160, 464.
3. M. Kobayashi, A. Sakurai, H. Saka and N. Takahashi, Plant Cell Physiol., 1989, 30, 963;
4. M. Kobayashi, P. Gaskin, C. R. Spray, Y. Suzuki, B. O. Phinney and J. MacMillan, Plant Physiol., 1993, 102, 379.
5. S. Fujioka, H. Yamane, C. R. Spray, M. Katsumi, B. O. Phinney, P. Gaskin, J. MacMillan and N. Takahashi, Proc. Natl. Acad. Sci. USA, 1988, 85, 903.
6. M. Kobayashi, P. Gaskin, C. R. Spray, Y. Suzuki, B. O. Phinney and J. MacMillan, Plant Physiol., 1993, 102, 379.
7. G. H. Posner, Org. Reactions (N. Y.), 1975, 22, 253;
8. B. H. Lipshutz and S. Sengupta, Org. Reactions (N. Y.), 1992, 41, 135.
9. M. Penny and C. L. Willis, J. Chem. Soc., Chem. Commun., 1993, 1111.
10. H. Gilman, R. G. Jones and L. A. Woods, J. Org. Chem., 1952, 17, 1630.
11. B. E. Cross, J. Chem. Soc., 1954, 4670.
12. J. MacMillan and C. L. Willis, J. Chem. Soc., Perkin Trans. 1, 1986, 309.
13. L. N. Mander, Personal Communication.
14. G. M. Whitesides, W. F. Fischer, Jr., J. San Fillipo, Jr., R. W. Bashe and H. O. House, J. Am. Chem. Soc., 1969, 91, 4871.
15. A. Cairncross and W. A. Sheppard, J. Am. Chem. Soc., 1968, 90, 2186.
16. G. A. Kraus and M. Kirihara, Tetrahedron Lett., 1992, 33, 7727.
17. B. H. Lipshutz and R. S. Wilhelm, J. Am. Chem. Soc., 1981, 103, 7672;
18. B. H. Lipshutz, Synlett, 1990, 119.
19. B. H. Lipshutz, R. S. Wilhelm, J. A. Kozlowski and D. A. Parker, J. Org. Chem., 1984, 49, 3928;
20. B. H. Lipshutz, R. S. Wilhelm and J. A. Kozlowski, Tetrahedron, 1984, 40, 5005.
21. D. B. Miller, J. Org. Chem., 1966, 31, 908;
22. J. P. Kennedy, J. Org. Chem., 1970, 35, 533;
23. J. P. Kennedy and S. Sivaram, J. Org. Chem., 1973, 38, 2262.
24. Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1986, 25, 947.
25. C. L. Willis, in Isotopes in the Physical and Biomedical Sciences, ed. J. R. Jones, Elsevier, Amsterdam, 1991, 223.
26. J. MacMillan and R. J. Pryce, J. Chem. Soc. (C), 1967, 740.
27. P. A. Bartlett and W. S. Johnson, Tetrahedron Lett., 1970, 4459.
28. J. MacMillan, Nat. Prod. Rep., 1997, 14, 221.
29. Y. Murakanni, Bot. Mag., 1968, 81, 33.
30. W. C. Still, M. Kahn and A. Mitra, J. Org. Chem., 1978, 43, 14.
31. J. C. W. Evans and C. F. H. Allen, Org. Synth., 1938, 18, 70.
32. W. G. Kofron and L. M. Baclawaski, J. Org. Chem., 1976, 41, 1879.
33. G. B. Kauffman and L. A. Teter, Inorg. Synth., 1963, 7, 9.
34. K. S. Albone, J. MacMillan, A. R. Pitt and C. L. Willis, Tetrahedron, 1986, 42, 3023.
35. D. F. Jones, J. F. Grove and J. MacMillan, J. Chem. Soc., 1964, 1835.