Collect. Czech. Chem. Commun.
2002, 67, 55-74
https://doi.org/10.1135/cccc20020055
Synthesis of Methoxynor Polyisoprenoid Alcohols by Alkylation of (3-Methoxyallyl)lithium Reagents
Qingwu Jin and Robert M. Coates*
Department of Chemistry, Roger Adams Laboratory, Box 40-5, University of Illinois, 600 South Mathews Avenue, Urbana, IL 61801, U.S.A.
References
1s. : Comprehensive Natural Products Chemistry, Vol. 2. Elsevier, Oxford 1999.
1a. Wise M. L., Croteau R.: “Monoterpene Biosynthesis”, Chap. 5.
1b. Cane D. E.: “Sesquiterpene Biosynthesis: Cyclization Mechanisms”.
1c. MacMillan J., Beale M. H.: “Diterpene Biosynthesis”, Chap. 8.
1d. Abe I., Prestwich G. D.: “Squalene Epoxidase and Oxidosqualene:Lanosterol Cyclase – Key Enzymes in Cholesterol Biosynthesis”, Chap. 10.
1e. Poralla K.: “Cycloartenol and Other Triterpene Cyclases”, Chap. 11.
2a. A. C., Angus R. H., Pierce A. M., Pierce H. D., Jr., Srinivasan R.: Biochemistry 1984, 23, 3582.
<https://doi.org/10.1021/bi00311a003>
2b. J. E., Abeles R. H.: Biochemistry 1986, 25, 5609.
<https://doi.org/10.1021/bi00367a040>
2c. M., Poulter C. D.: Biochemistry 1988, 27, 7315.
<https://doi.org/10.1021/bi00419a021>
2d. A., Taton M., Benveniste P.: Biochem. Soc. Trans. 1990, 18, 48.
<https://doi.org/10.1042/bst0180048>
2e. P., Pyun H.-J., Coates R. M., Croteau R.: Arch. Biochem. Biophys. 1992, 299, 63.
<https://doi.org/10.1016/0003-9861(92)90244-Q>
2f. A., Pyun H.-J., Coates R. M.: J. Org. Chem. 1992, 57, 3444.
<https://doi.org/10.1021/jo00038a038>
2g. R. J., Ravn M. M., Coates R. M., Croteau R. B.: J. Am. Chem. Soc. 2001, 123, 8974.
<https://doi.org/10.1021/ja010670k>
3a. I., Rohmer M., Prestwich G. D.: Chem. Rev. 1993, 93, 2189.
<https://doi.org/10.1021/cr00022a009>
3b. I., Tomesch J. C., Wattanasin S., Prestwich G. D.: Nat. Prod. Rep. 1994, 11, 279.
<https://doi.org/10.1039/np9941100279>
4a. C. J., Croteau R. B.: Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 4856.
<https://doi.org/10.1073/pnas.84.14.4856>
4b. C. J., Croteau R.: Arch. Biochem. Biophys. 1986, 246, 733.
<https://doi.org/10.1016/0003-9861(86)90330-9>
4c. D. E., Tzantrizos Y. S.: J. Am. Chem. Soc. 1996, 118, 10037.
<https://doi.org/10.1021/ja961981b>
4d. D. E., Yang G.: J. Org. Chem. 1994, 59, 5794.
<https://doi.org/10.1021/jo00098a046>
4e. M. M., Coates R. M., Flory J. E., Peters R. J., Croteau R.: Org. Lett. 2000, 2, 573.
<https://doi.org/10.1021/ol991230p>
5. K. A., Starks C. M., Noel J. P., Chappell J.: J. Am. Chem. Soc. 2000, 122, 1861.
<https://doi.org/10.1021/ja993584h>
6. E. J., Virgil S. C.: J. Am. Chem. Soc. 1991, 113, 4025.
<https://doi.org/10.1021/ja00010a073>
7. D. C., Carroll B. J., Jin Q., Rithner C., Lenger S. R., Floss H. G., Coates R. M., Williams R. M., Croteau R.: Chem. Biol. 2000, 7, 969.
<https://doi.org/10.1016/S1074-5521(00)00046-6>
8a. R. E., Mueller R. H., Willard A. K.: J. Org. Chem. 1976, 41, 986.
<https://doi.org/10.1021/jo00868a018>
8b. R. E., Mueller R. H., Willard A. K.: J. Am. Chem. Soc. 1976, 98, 2868.
<https://doi.org/10.1021/ja00426a033>
8c. V., Massias F., Uguen D.: Tetrahedron Lett. 1989, 30, 7389.
<https://doi.org/10.1016/S0040-4039(00)70705-2>
8d. T., Takai K., Oshima K., Utimoto K.: J. Org. Chem. 1987, 52, 4410.
<https://doi.org/10.1021/jo00228a055>
8e. R. J., Henrick C. A., Siddall J. B., Zurfluh R.: J. Am. Chem. Soc 1972, 94, 5379.
<https://doi.org/10.1021/ja00770a039>
8f. T., Sasada Y., Ohtani T., Asada T., Kinoshita H., Senda H., Inomata K.: Bull. Chem. Soc. Jpn. 1992, 65, 75.
<https://doi.org/10.1246/bcsj.65.75>
9a. D. A., Andrews G. C., Buckwalter B: J. Am. Chem. Soc. 1974, 96, 5560.
<https://doi.org/10.1021/ja00824a039>
9b. W. C., MacDonald T. L.: J. Am. Chem. Soc. 1974, 96, 5561.
<https://doi.org/10.1021/ja00824a040>
9c. W. C., MacDonald T. L.: J. Org. Chem. 1976, 41, 3620.
<https://doi.org/10.1021/jo00884a031>
10. E., Zoltobroda G., Langlois Y.: Tetrahedron Lett. 2000, 41, 337.
<https://doi.org/10.1016/S0040-4039(99)02086-9>
11a. D., Weber W. P.: J. Org. Chem. 1981, 46, 265.
<https://doi.org/10.1021/jo00315a007>
11b. After completion of this work, ether 15 was reported, albeit without a preparative procedure, literature reference, or characterization data. See T. R., Zhao H.: Org. Lett. 1999, 1, 1123.
<https://doi.org/10.1021/ol990947+>
12. E. P., Heathcock C. H.: J. Am. Chem. Soc. 1987, 109, 3353.
<https://doi.org/10.1021/ja00245a027>
13. R. C., Lett R. M.: J. Org. Chem. 1982, 47, 2268.
<https://doi.org/10.1021/jo00133a007>
14. A., Hayashi T., Hori I., Jindo Y., Oishi T.: Synthesis 1978, 370.
<https://doi.org/10.1055/s-1978-24749>
15. L. J., Ash L., Marson S.: Synthesis 1974, 129.
<https://doi.org/10.1055/s-1974-23262>
16. Y.: J. Org. Chem. 1980, 45, 4097.
<https://doi.org/10.1021/jo01309a006>
17. R. E., Norbeck D. W.: J. Org. Chem. 1985, 50, 2198.
<https://doi.org/10.1021/jo00212a041>
18a. E. W., Meyers A. I.: J. Org. Chem. 1971, 36, 3044.
18b. R. M., Jin A. Q.: J. Org. Chem. 1997, 62, 7475.
<https://doi.org/10.1021/jo9706335>
19. P., Brown R. A.: J. Org. Chem. 1982, 47, 34.
<https://doi.org/10.1021/jo00340a008>
20. R. M., Ley D. A., Cavender P. L.: J. Org. Chem. 1978, 43, 4915.
<https://doi.org/10.1021/jo00420a003>
21. Woodside A. B., Huang Z., Poulter C. D.: Org. Synth. 1993, Coll. Vol. VIII, 616.
22. We are grateful to D. C. Williams and R. Croteau at Washington State University for carrying out the preliminary incubations with taxadiene synthase and the GC/MS analyses of the products.
23. The hydrolysis of diphosphate 7 was effected by reaction with 0.2 M HCl followed by dehydration in refluxing 1,2-dichloroethane containing pyridinium p-toluenesulfonate to produce a mixture of products containing the expected nonadecatetraenone isomers according to NMR analysis.
24. Rigaudy J., Klesney S. P.: Nomenclature of Organic Chemistry, Sections A–H. Pergamon Press, Oxford 1979.
25. G. B., Teter L. A.: Inorg. Synth. 1963, 7, 9.
<https://doi.org/10.1002/9780470132388.ch3>
26. J.: J. Org. Chem. 1989, 54, 509.
<https://doi.org/10.1021/jo00263a052>
27. W. C., Kahn M., Mitra A.: J. Org. Chem. 1978, 43, 2923.
<https://doi.org/10.1021/jo00408a041>
28. D., Chauvin Y.: Bull. Soc. Chim. Fr. 1974, 652.
29. R., Saucy G.: Helv. Chim. Acta 1967, 50, 2095.
<https://doi.org/10.1002/hlca.19670500746>
30. A., McGuirk P. R., Helquist P.: J. Org. Chem. 1979, 44, 3888.
<https://doi.org/10.1021/jo01336a029>
31. B. B., Rodini D. J., Van Straten J.: J. Am. Chem. Soc. 1980, 102, 5872.
<https://doi.org/10.1021/ja00538a028>
32. J. M., Garland R. P., Hartshorn M. P.: Aust. J. Chem. 1972, 25, 947.
<https://doi.org/10.1071/CH9720947>
33. C., Töke L., Kolonits P.: J. Org. Chem. 1966, 31, 1447.
<https://doi.org/10.1021/jo01343a030>
34. I., Doi Y.: Tetrahedron Lett. 1972, 1163.
<https://doi.org/10.1016/S0040-4039(01)84535-4>
35. J. M., Poulter C. D.: Tetrahedron 1996, 52, 119.
<https://doi.org/10.1016/0040-4020(95)00909-R>
36. C. B., MacSweeney D. F., Ramage R.: Tetrahedron 1971, 27, 1491.
<https://doi.org/10.1016/S0040-4020(01)98014-7>
37. J. A., Trometer J. D., Blough B. E., Crute T. D.: J. Org. Chem. 1988, 53, 4274.
<https://doi.org/10.1021/jo00253a020>
38. Lange N. A. (Ed.): Lange’s Handbook of Chemistry, 8th ed., p. 939. Handbook Publishers, Inc., Sandusky (OH) 1952.

