Synthesis of allylic isoprenoid diphosphates by S(N)2 displacement of diethyl phosphate

European Journal of Organic Chemistry

Volumn , Issue 8, 2000, Pages 1401-1410

  Ravn, Matthew M ^a   Jin, Qingwu ^a   Coates, Robert M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Asymmetric labeling; Deuterium labeling; Enzyme inhibitors; Phosphorylations; Terpenoid biosynthesis

Indexed keywords

ALLYL COMPOUND; BORANE DERIVATIVE; GERANIOL; ISOPRENOID; PHOSPHATE; PYROPHOSPHATE; TERPENOID;

ARTICLE; BIOSYNTHESIS; CHEMICAL LABELING; CHEMICAL MODIFICATION; CONFORMATIONAL TRANSITION; ENZYME SUBSTRATE; PHOSPHORYLATION; STEREOISOMERISM;

EID: 0034102478     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(200004)2000:8<1401::AID-EJOC1401>3.0.CO;2-P     Document Type: Article

References (80)

1. Isoprenoids Including Carotenoids and Steroids (Ed.: D. E. Cane), vol. 2, in: Comprehensive Natural Products Chemistry (Eds.: D. H. R. Barton, K. Nakanishi, O. Meth-Cohn), Pergamon Press, Oxford, England, 1999.
2. Biosynthesis of Isoprenoid Compounds (Eds.: J. W. Porter, S. L. Spurgeon), Wiley, New York, USA, vol. 1, 1981; vol. 2, 1983.
3. [3a] F. Cramer, W. Rittersdorf, Tetrahedron 1967, 23, 3015-3022.
4. [3b] W. Rittersdorf, F. Cramer, Tetrahedron 1967, 23, 3023-3028.
5. [3c] P. Valenzuela, O. Cori, Tetrahedron Lett. 1967, 3089-3094.
6. [3d] B. K. Tidd, J. Chem. Soc. B 1971, 1168-1176.
7. [3e] D. N. Brems, H. C. Rilling, J. Am. Chem. Soc. 1977, 99, 8351-8352.
8. [4a] J. E. Reardon, R. H. Abeles, Biochemistry 1986, 25, 5609-5616.
9. [4b] M. Meuhlbacher, C. D. Poulter, Biochemistry 1988, 27, 7315-7328.
10. [4c] A. Steiger, H.-J. Pyun, R. M. Coates, J. Org. Chem. 1992, 57, 3444-3449.
11. [4d] A. Koohang, R. M. Coates, D. Owen, C. D. Poulter, J. Org. Chem. 1999, 64, 6-7.
12. [5a] G. Popják, Methods Ezymol. 1969, 15, 393-454.
13. [5b] R. R. Fall, C. A. West, J. Biol. Chem. 1971, 246, 6913-6928.
14. [5c] D. E. Cane, D. B. McIlwaine, J. S. Oliver, J. Am. Chem. Soc., 1990, 112, 1285-1286.
15. [5d] D. J. Christensen, C. D. Poulter, Biorg. Med. Chem. 1994, 2, 631-637.
16. For a summary and leading references see: V. J. Davisson, A. B. Woodside, T. R. Neal, K. E. Stremler, M. Muehlbacher, C. D. Poulter, J. Org. Chem. 1986, 51, 4768-4779.
17. [7a] F. Cramer, W. Böhm, Angew. Chem. 1959, 71, 775.
18. [7b] F. Cramer, W. Rittersdorf, W. Böhm, Justus Liebigs Ann. Chem. 1962, 654, 180-188.
19. [7c] R. H. Cornforth, G. Popják, Methods Enzymol. 1969, 15, 359-390.
20. [8a] L. L. Danilov, T. N. Druzhinina, N. A. Kalinchuk, S. D. Maltsev, V. N. Shibaev, Chem. Phys. Lipids 1989, 51, 191-203.
21. [8b] L. L. Danilov, S. D. Maltsev, V. N. Shibaev, Bioorg. Khim. (Engl. Transl.) 1991, 16, 814-816.
22. [9a] V. J. Davisson, A. B. Woodside, C. D. Poulter, Methods Enzymol. 1985, 110A, 130-144.
23. [9b] A. B. Woodside, Z. Huang, C. D. Poulter, Org. Synth. Coll. Vol. 1993, 8, 616-620.
24. [9c] V. J. Davisson, T. M. Zabriskie, C. D. Poulter, Bioorg. Chem. 1986, 14, 46-54.
25. [10a] D. E. Cane, Tetrahedron 1980, 36, 1109-1159.
26. [10b] K. A. Drengler, R. M. Coates, J. Chem. Soc., Chem. Commun. 1980, 856-857.
27. [10c] W. J. Guilford, R. M. Coates, J. Am. Chem. Soc. 1982, 104, 3506-3508.
28. [10d] R. M. Coates, P. L. Cavender, J. Am. Chem. Soc. 1980, 102, 6358-6359.
29. [10e] D. E. Cane, Acc. Chem. Res. 1985, 18, 220-226.
30. [11a] R. L. Edelstein, V. A. Weller, M. D. Distefano, J. S. Tung, J. Org. Chem. 1998, 63, 5298-5299.
31. [11b] Y.-Q. Mu, C. A. Omer, R. A. Gibbs, J. Am. Chem. Soc. 1996, 118, 1817-1823.
32. [11c] V. J. Davisson, C. D. Poulter, J. Am. Chem. Soc. 1993, 115, 1245-1260.
33. J. A. Miller, H. C. S. Wood, J. Chem. Soc. C 1968, 1837-1843.
34. [13a] R. C. Haley, J. A. Miller, H. C. S. Wood, J. Chem. Soc. C 1969, 264-268.
35. [13b] Y. Kitagawa, S. Hashimoto, S. Iemura, H. Yamamoto, H. Nozaki, J. Am. Chem. Soc. 1976, 98, 5030-5031.
36. [13c] Y. Tanigawa, K. Nishimura, A. Kawasaki, S.-I. Murahashi, Tetrahedron Lett. 1982, 23, 5549-5552.
37. [13d] S.-I. Murahashi, Y. Taniguchi, Y. Imada, Y. Tanigawa, J. Org. Chem. 1989, 54, 3292-3303.
38. [13e] S. Nowotny, C. E. Tucker, C. Jubert, P. Knochel, J. Org. Chem. 1995, 60, 2762-2772.
39. [14a] J. A. Marshall, J. D. Trometer, B. E. Blough, T. D. Crute, J. Org. Chem. 1988, 53, 4274-4282.
40. [14b] E. J. Leopold, Org. Synth. Coll. Vol. 1990, VII, 258-263.
41. [15a] M. M. Midland, Chem. Rev. 1989, 89, 1553-1561.
42. [15b] M. M. Midland, S. Greer, A. Tramontano, S. A. Zderic, J. Am. Chem. Soc. 1979, 101, 2352-2355.
43. [15c] P. C. Prabhakaran, S. J. Gould, G. R. Orr, J. K. Coward, J. Am. Chem. Soc. 1988, 110, 5779-5784.
44. 1]geraniol may also be accomplished with (S)-1,1-binaphthyloxy ethoxy aluminum hydride, albeit with lower enantioselectivity; see: M. Nishizawa; R. Noyori, Tetrahedron. Lett. 1980, 21, 2821-2824.
45. [17a] S. Krishnamurthy, H. C. Brown, J. Org. Chem. 1977, 42, 1197-1201.
46. [17b] M. M. Midland, R. S. Graham, Org. Synth. Coll. Vol. 1990, VII, 402-406.
47. [18a] H. Gerlach, B. Zagalak, J. Chem. Soc., Chem. Commun. 1973, 274-275.
48. [18b] H. Gerlach, D. Kappes, R. K. Boeckman, Jr., G. N. Maw, Org. Synth., Coll. Vol. 1998, 9, 151-154.
49. Line shape simulations and area calculations were carried out using the NMR Utility Transform Software (NUTS) for WINDOWS 95/NT purchased from Acorn NMR Inc., 46560 Fremont Blvd., #418, Fremont, CA 94538-6491, USA.
50. J.-H. Yang, T. M. Zabriskie, C. D. Poulter, J. Chromatog. 1984, 312, 121-132.
51. [21a] S. S. Sofer, H. C. Rilling, J. Lipid Res. 1969, 10, 183-187.
52. [21b] R. M. Coates, H.-K. Kang, J. Org. Chem. 1987, 52, 2065-2074.
53. D. Zhang, C. D. Poulter, Anal. Biochem. 1993, 213, 356-361.
54. Lange's Handbook of Chemistry, 11th ed. (Ed.: J. A. Dean), McGraw-Hill, New York, USA, 1972, Part 5, pp. 15-25.
55. [24a] M. Hezari, N. G. Lewis, R. Croteau, Arch. Biochem. Biophys. 1995, 322, 437-444.
56. [24b] M. R. Wildung, R. Croteau, J. Biol. Chem. 1996, 271, 9201-9204.
57. J. MacMillan, M. H. Beale, Diterpene Biosynthesis, chapter 8 in ref.[1]
58. [26a] R. E. LaFever, B. S. Vogel, R. Croteau, Arch. Biochem. Biophys. 1994, 313, 139-149.
59. [26b] B. S. Vogel, M. R. Wildung, G. Vogel, R. Croteau, J. Biol. Chem. 1996, 271, 23262-23268.
60. [27a] M. M. Ravn, R. M. Coates, R. Jetter, R. B. Croteau, Chem. Commun. 1998, 21-22.
61. [27b] M. M. Ravn, R. M. Coates, J. E. Flory, R. J. Peters, R. Croteau, Org. Lett., in press.
62. 4, aqueous acetone (60% for 2 steps).
63. E. W. Collington, A. I. Meyers, J. Org. Chem. 1971, 36, 3044-3045.
64. J. W. Huffman, R. C. Desai, J. E. LaPrade, J. Org. Chem. 1983, 48, 1474-1479.
65. For reviews on aza analog inhibitors of oxidosqualene cyclase see: [31a] I. Abe, G. D. Prestwich, "Squalene Epoxidase and Oxidosqualene: Lanosterol Cyclase, Key Enzymes in Cholesterol Biosynthesis", chapter 10 in ref.[1] [31b] I. Abe, M. Rohmer, G. D. Prestwich, Chem. Rev. 1993, 93, 2189-2206.
66. For reviews on aza analog inhibitors of oxidosqualene cyclase see: [31a] I. Abe, G. D. Prestwich, "Squalene Epoxidase and Oxidosqualene: Lanosterol Cyclase, Key Enzymes in Cholesterol Biosynthesis", chapter 10 in ref.[1] [31b] I. Abe, M. Rohmer, G. D. Prestwich, Chem. Rev. 1993, 93, 2189-2206.
67. [32a] R. S. Mohan, N. K. N. Yee, R. M. Coates, Y.-Y. Ren, P. Stamenkovic, I. Mendez, C. A. West, Arch. Biochem. Biophys. 1996, 330, 33-47.
68. [32b] N. K. N. Yee, R. M. Coates, J. Org. Chem. 1992, 57, 4598-4608.
69. [33a] J. D. Duncan, C. A. West, Plant Physiol. 1981, 68, 1128-1134.
70. [33b] T.-P. Sun, Y. Kamiya, Plant Cell 1994, 6, 1509-1518.
71. [33c] T.-P. Sun, H. M. Goodman, F. M. Ausubel, Plant Cell 1992, 4, 119-128.
72. S.-I. Takanashi, K. Mori, Liebigs Ann. 1997, 825-838.
73. E. E. Van Tamelen, R. G. Nadeau, Bioorg. Chem. 1982, 11, 197-218.
74. O. Hoshino, M. Ishizaki, S. Sawaki, M. Yuasa, B. Umezawa, Chem. Pharm. Bull. 1988, 36, 3373-3380.
75. C. W. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
76. [38a] D. R. Burfield, R. H. Smithers, J. Org. Chem. 1978, 43, 3966-3968.
77. [38b] D. R. Burfield, K.-H. Lee, R. H. Smithers, J. Org. Chem. 1977, 42, 3060-3065.
78. E. J. Corey, N. W. Gilman, B. E. Ganem, J. Am. Chem. Soc., 1968, 90, 5616-5617.
79. N. Ya Grigor'eva, I. M. Avrutov, A. V. Semenovskii, V. N. Odinokov, V. R. Akhunova, G. A. Tolstikov, Akad. Nauk. Sci. Bull. (Engl.) 1979, 28, 353-358.
80. N. Khan, D. E. Loeber, T. P. Taube, B. C. Weedon, J. Chem. Soc., Perkin Trans. 1 1975, 1457-1464.