Unusual reactions of methylsulfonyl esters: Syntheses of 3α-methyl and 3β-methyl gibberellin A20

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1997, Pages 433-442

  Beale, Michael H ^a   Loaring, Huw ^a   Peakman, Torren ^a   Penny, Martin ^a   Willis, Christine L ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748662448     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605570b     Document Type: Article

References (33)

1. T. J. Ingram, J. B. Reid and J. MacMillan, Planta, 1986, 168, 414;
2. S. Fujioka, H. Yamane, C. R. Spray, P. Gaskin, J. MacMillan, B. O. Phinney and N. Takahashi, Plant Physiol., 1988, 88, 1367;
3. M. Kobayashi, A. Sakurai, H. Saka and N. Takahashi, Plant Cell Physiol., 1989, 30, 963;
4. M. Nakayama, H. Yamane, N. Murofushi, N. Takahasi, L. N. Mander and H. Seto, J. Plant Growth Regul., 1991, 10, 115.
5. T. J. Ingram, J. B. Reid, I. C. Murfet, P. Gaskin, C. L. Willis and J. MacMillan, Planta, 1984, 160, 455;
6. C. R. Spray, B. O. Phinney, P. Gaskin, S. J. Gilmour and J. MacMillan, Planta, 1984, 160, 464.
7. S. Fujioka, H. Yamane, C. R. Spray, B. O. Phinney, P. Gaskin, J. MacMillan and N. Takahashi, Plant Physiol., 1990, 94, 127;
8. N. Murofushi, I. Honda, R. Hirasawa, I. Yamaguchi, N. Takahashi and B. O. Phinney, Agric. Biol. Chem., 1991, 55, 435.
9. K. S. Albone, P. Gaskin, J. MacMillan, V. A. Smith and J. Weir, Planta, 1989, 177, 108;
10. K. S. Albone, P. Gaskin, J. MacMillan and C. L. Willis, Plant Physiol., 1990, 94, 132.
11. M. H. Beale and J. MacMillan, Phytochemistry, 1981, 20, 693;
12. G. V. Hoad, B. O. Phinney, V. M. Sponsel and J. MacMillan, Phytochemistry, 1981, 20, 703.
13. T. Saito, Y. Kamiya, H. Yamane, A. Sakurai, N. Murofushi and N. Takahashi, Biosci, Biotechnol. Biochem., 1992, 56, 1046.
14. K. S. Albone, J. MacMillan, A. R. Pitt and C. L. Willis, Tetrahedron, 1986, 42, 3203.
15. M. H. Beale and J. MacMillan, J. Chem. Soc., Perkin Trans. 1, 1980, 877.
16. E. Keinan and P. A. Gleize, Tetrahedron Lett., 1982, 23, 477.
17. J. W. Cornforth, R. H. Cornforth and K. K. Mathew, J. Chem. Soc., 1959, 112.
18. C. R. Johnson, R. W. Herr and D. M. Wieland, J. Org. Chem., 1973, 38, 4263 and references cited therein;
19. Y. Yamamoto, Angew. Chem., Int. Ed. Engl., 1986, 25, 947;
20. A. Alexakis, D. Jachiet and J. F. Normant, Tetrahedron, 1986, 42, 5607.
21. B. H. Lipshutz and S. Sengupta, Org. React. (N. Y.), 1992, 41, 135;
22. B. H. Lipshutz, R. S. Wilhelm, J. A. Kozlowski and D. A. Parker, J. Org. Chem., 1984, 49, 3928.
23. G. H. Posner, Org. React. (N. Y.), 1975, 22, 253;
24. C. Huynh, G. Linstrumelle and F. Derguini-Bouchmechal, Tetrahedron Lett., 1979, 1503.
25. M. Fukumasa, K. Furuhashi, J. Umezawa, O. Takahashi and T. Hirai, Tetrahedron Lett., 1991, 32, 1059.
26. C. R. Johnson and G. A. Outra, J. Am. Chem. Soc., 1973, 95, 7777 and 7783.
27. M. Penny and C. L. Willis, J. Chem. Soc., Chem. Commun., 1993, 1111.
28. A. Calvo-Mateo, M. J. Camarasa, A. Diaz-Ortiz and F. G. de las Heras, J. Chem. Soc., Chem. Commun., 1988, 114.
29. M. F. Reich, V. J. Lee, J. Ashcroft and G. O. Morton, J. Org. Chem., 1993, 58, 5288.
30. E. J. Corey, T. M. Brennam and R. L. Carney, J. Am. Chem. Soc., 1971, 93, 7318.
31. D. H. Barton, D. O. Jang and J. C. Jaszberenyi, Tetrahedron Lett., 1992, 33, 2311.
32. K. Hanson, J. A. O'Neill, T. J. Simpson and C. L. Willis, J. Chem. Soc., Perkin Tram 1, 1994, 2493.
33. Y. Murakami, Bot. Mag., 1968, 81, 33.