A synthesis of taxusin

Journal of the American Chemical Society

Volumn 110, Issue 19, 1988, Pages 6558-6560

  Holton, Robert A ^a   Juo, R R ^a   Kim, Hyeong B ^a   Williams, Andrew D ^a   Harusawa, Shinya ^a   Lowenthal, Richard E ^a   Yogai, Sadamu ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXUSIN; UNCLASSIFIED DRUG;

DRUG SYNTHESIS; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0023694803     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00227a043     Document Type: Article

References (17)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggan, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325. (b) Miller, R. W.; Powell, R. G.; Smith, C. R., Jr. J. Org. Chem. 1981, 46, 1469 and references contained therein.
2. For leading references, see: (a) Manfredi, J. J.; Fant, J.; Horwitz, S. B. Eur. J. Cell Biol. 1986, 42, 126. (b) Solari, A. J.; Duschak, V. G. Micro Sc. Electron. Biol. Cel. 1985, 9, 163. (c) Bhattacharyya, B.; Ghoschaudhuri, G.; Maity, S.; Biswas, B. B. Ann. N. Y. Acad. Sci. 1986, 466, 791. (d) Horwitz, S. B.; Lothstein, L.; Manfredi, J. J.; Melcado, W.; Parness, J.; Roy, S. N.; Schiff, P. B.; Sorbara, L.; Zeheb, R. Ann. N. Y. Acad. Sci. 1986, 466, 733. (e) Wallin, M.; Nordh, J.; Deinum, J. Biochim. Biophys. Acta 1986, 880, 189.
3. For leading references, see: (a) Riondel, J.; Jacrot, M.; Picot, F.; Beriel, H.; Mouriquand, C.; Potier, P. Cancer Chemother. Pharmacol. 1986, 17, 137. (b) Manfredi, J. J.; Horwitz, S. B. Pharmacol. Ther. 1984, 25, 83. (c) Hamel, E.; Lin, C. M.; Johns, D. G. Cancer Treat. Rep. 1982, 66, 1381. (d) Stiffness, M.; Douros, J. D. Methods Cancer Res. 1979, 16, 73. (e) Fuchs, D. A.; Johnson, R. K. Cancer Treat. Rep. 1978, 62, 1219. (f) Schiff, P. B.; Horwitz, S. B. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 1561.
4. Large scale isolation: Boettner, F.; Williams, M.; Boyd, R.; Halpern, B. D., preparation Report 9 on Contract N01-CM-77070, N.C.I.
5. A large number of articles describing this situation have appeared in U. S. and Canadian newspapers and magazines. For leading references, see: (a) The New York Times, 1987, May 3, I, 29:1. (b) Strycker, L. The Register-Guard (Eugene, OR), 1987, 120 (166), 1B. (c) Brooks, B. Tallahassee Democrat (FL) 1987, 82 (270), 1E. (d) Audubon, 9/87. (e) Boling, R. Equinox 1988, 37, 7:1, 107.
6. Review: Miller, R. W. J. Nat. Prod. 1980, 43, 425.
7. Synthetic studies from over 20 different laboratories have been described. See: (a) Swindell, C. S.; Patel, B. P. Tetrahedron Lett. 1987, 28, 5275. (b) Kraus, G.; Thomas, P. J.; Hon, Y. S. J. Chem. Soc., Chem. Commun. 1987, 1849. (c) Pettersson, L.; Frejd, T.; Magnusson, G. Tetrahedron Lett. 1987, 28, 2753. (d) Wender, P. A.; Snapper, M. L. Tetrahedron Lett. 1987, 28, 2221. (e) Kende, A. S.; Johnson, S.; Sanfilippo, P.; Hodges, J. C.; Jungheim, L. N. J. Am. Chem. Soc. 1986, 108, 3513. (f) Winkler, J. D.; Hey, J. P. J. Am. Chem. Soc. 1986, 108, 6425 and references cited therein.
8. Miyazaki, M.; Shimizu, K.; Mishima, H.; Kurabayashi, M. Chem. Pharm. Bull. 1968, 16, 546. (b) Liu, C. L.; Lin, Y. C.; Lin, Y. M.; Chen, F. C. Tai-wan K'o Hsueh 1984, 38, 119. (c) Erdtman, H.; Tsuno, K. Phytochemistry 1969, 8, 931. (d) Lee, C. L.; Hirose, Y. Nakatsuka Mokuzai Gakkaishi 1975, 21, 249. (e) Chan, W. R.; Halsall, T. G.; Hornby, G. M.; Oxford, A. W.; Sabel, W.; Bjamer, K.; Ferguson, G.; Robertson, J. M. J. Chem. Soc., Chem. Commun. 1966, 923.
9. Holton, R. A. J. Am. Chem. Soc. 1984, 106, 5731.
10. Holton, R. A.; Kennedy, R. M. Tetrahedron Lett. 1984, 25, 4455.
11. Diol 6 is the kinetic product of this rearrangement: Holton, R. A.; Juo, R. R.; Lowenthal, R. E.; Goedken, V., manuscript in preparation.
12. Reich, H. J.; Renga, J. M.; Reich, I. L. J. Am. Chem. Soc. 1975, 97, 5434.
13. For example, see: Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
14. Baldwin, J. E.; Hofle, G. A.; Lever, Jr., O. W. J. Am. Chem. Soc. 1974, 96, 7125.
15. 2. Holton, R. A.; Williams, A. D., submitted for publication. (b) Molander, G. A.; Hahn, G. J. Org. Chem. 1986, 51, 1135. (c) White, J. D.; Somers, T. C. J. Am. Chem. Soc. 1987, 109, 4424.
16. Ganem, B.; Small, Jr., V. R. J. Org. Chem. 1974, 39, 3728. (b) Gross, R. S.;Watt, D. A. Synth. Commun. 1987, 17, 1749.
17. Buchi, G.; MacLeod, W. D., Jr.; Padilla, J. J. Am. Chem. Soc. 1964, 86, 4438.