Taxadiene synthase-catalyzed cyclization of 6-fluorogeranylgeranyl diphosphate to 7-fluoroverticillenes

Journal of the American Chemical Society

Volumn 127, Issue 21, 2005, Pages 7834-7842

  Jin, Yinghua ^a   Williams, David C ^b   Croteau, Rodney ^b   Coates, Robert M ^a  

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

^b WASHINGTON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ELECTRONS; ENZYMES; GAS CHROMATOGRAPHY; HYDROCARBONS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CYCLIZATION; DITERPENES; PROTON TRANSFER;

PHOSPHATES;

4 IODOBENZOIC ACID; DITERPENE; FLUORINE; GERANYLGERANYL PYROPHOSPHATE; METHYLENE 7 FLUOROVERTICILLENE; SYNTHETASE; TAXADIENE SYNTHASE; UNCLASSIFIED DRUG; VERTICILLEN 12 YL; VERTICILLOL; VERTICILLOL 4 IODOBENZOATE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CIRCULAR DICHROISM; CRYSTAL STRUCTURE; CYCLIZATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; DITERPENES; HYDROCARBONS, FLUORINATED; ISOMERASES; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POLYISOPRENYL PHOSPHATES; STEREOISOMERISM;

EID: 19744366357     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja050592r     Document Type: Article

References (89)

1. (a) Kingston, D. G. I.; Molinero, A. A.; Rimoldi, J. M. The Taxane Diterpenoids. In Progress in the Chemistry of Organic Natural Products: Herz, W., Kirby, G. W., Moore, R. E., Steglich, W., Tamm. Ch., Eds.: Springer-Verlag: Wien, New York, 1993; Vol. 61. pp 1-189.
2. (b) Miller, R. W. J. Nat. Prod. 1980, 43, 425-437.
3. (c) Guçritte-Voegelein, F.; Guȩnard, D.; Potier, P. J. Nat. Prod. 1987, 50, 9-18.
4. (d) Blechert, S.; Guenard, S. Taxus Alkaloids. In The Alkaloid's. Chemistry and Pharmacology; Brossi, A., Ed.: Academic Press: New York, 1990; Vol. 39. pp 195-238.
5. (a) Baxter, J. N.; Lythgoe, B.; Scales, B.; Serowston, R. M.; Trippett, S. J. Chem. Soc. 1962, 2964-2971.
6. (b) Lunaglcey, B. W.; Lythgoe, B.; Scales, B.; Scrowston, R. M.; Trippett, S.; Wray, D. J. Chem. Soc. 1962, 2972-2984.
7. (c) Harrison, J. W.; Lythgoe, B. J. Chem. Soc. C 1966, 1932-1933.
8. (d) Harrison, J. W.; Scrowston, R. M.; Lythgoe, B. J. Chem. Soc. C 1966, 1933-1945.
9. (e) Lythgoe, B. Taxus Alkaloids. In The Alkaloids. Chemistry and Physiology; Manske, R. H. F., ed.; Academic Press: New York, 1968; Vol. 10, pp 547-627.
10. (a) Kurono, M.; Nakadaira, Y.; Onuma, S.; Sasaki, K.; Nakanishi, K. Tetrahedron Lett. 1963, 4, 2153-2160.
11. (b) Nakanishi, K.; Kurono, M.; Bhacca, N. S. Tetrahedron Lett. 1963, 4, 2161-2165.
12. (c) Ueda, K.; Uyeo, S.; Yamamoto, Y.; Maki, Y. Tetrahedron Lett. 1963, 4, 2167-2171.
13. (d) Kurono, M.; Maki, Y.; Nakanishi, K.; Ohashi, M.; Ueda, K. Uyeo, S.; Woods, M. C.; Yamamoto, Y. Tetrahedron Lett. 1965, 6, 1917-1926.
14. (e) Shiro, M.; Sato, T.; Koyama, H.; Maki, Y.; Nakanishi, K.; Uyeo, S. Chem. Commun. 1966, 97-98.
15. (f) Shiro, M.; Koyama, H. J. Chem. Soc. B 1971, 1342-1346.
16. (g) Harada, N.; Ohashi, M.; Nakanishi, K. J. Am. Chem. Soc. 1968, 90, 7349-7351.
17. (h) Harada, N.; Nakanishi, K. J. Am. Chem. Soc. 1969, 91, 3989-3991.
18. (a) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1597-1598.
19. (b) Holton, R. A. et al. J. Am. Chem. Soc. 1994, 116, 1599-1600.
20. (a) Nicolaou, K. C. et al. Nature 1994, 367., 630-634.
21. (b) Nicolaou, K. C.; Nantermet, P. G.; Ueno, H.; Guy, R. K.; Couladouros, E. A.; Sorensen, E. J. J. Am. Chem. Soc. 1995, 117, 624-633.
22. (c) Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Sorensen, E. J.; Claiborne, C. F.; Guy, R. K.; Hwang, C.-K.; Nakada, M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634-644.
23. (d) Nicolaou, K. C.; Yang, Z.; Liu, J.-J.; Nantermet, P. G.; Claiborne, C. F.; Renaud, J.; Guy, R. K.; Shibayama, K. J. Am. Chem. Soc. 1995, 117, 645-652.
24. (e) Nicolaou, K. C.; Ueno, H.; Liu, J.-J.; Nantermet, P. G.; Yang, Z.; Renaud, J.; Paulvannan, K.; Chadha, R. J. Am. Chem. Soc. 1995, 117, 653-659.
25. (a) Maters, J. J.; Link, J. T.; Snyder, L. B.; Young, W. B.; Danishefsky, S. J. Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
26. (b) Danishefsky, S. J. et al. J. Am. Chem. Soc. 1996, 118, 2843-2859.
27. (a) Wender, P. A. et al. J. Am. Chem. Soc. 1997, 119, 2755-2756.
28. (b) Wender, P. A. et al. J. Am. Chem. Soc. 1997, 119, 2757-2758.
29. (a) Morihira, K.; Hara, R.; Kawahara, S.; Nishimori, T.; Nakamura, N.; Kusama, H.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 12980-12981.
30. (b) Kusama, H.; Hara, R.; Kawahara, S.; Nishimori, T.; Kashima, H.; Nakamura, N.; Morihira, K.; Kuwajima, I. J. Am. Chem. Soc. 2000, 122, 3811-3820.
31. Mukaiyama, T.; Shiina, I.; Iwadare, H.; Saitoh, M.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Tani, Y.; Hasegawa, M.; Yamada, K.; Saitoh, K. Chem. Eur. J. 1999, 5, 121-161.
32. (a) Wani, M. C.; Taylor, H. L.; Wall, M. E. J. Am. Chem. Soc. 1971, 93, 2325-2327.
33. (b) Mastropaolo, D.; Camerman, A.; Luo, Y.; Brayer, G. D.; Camerman, N. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6920-6924.
34. (c) Gao, Q.; Parker, W. L. Tetrahedron 1996, 52, 2291-2300.
35. Erdtman, H.; Norin, T.; Sumimoto, M.; Morrison, A. Tetrahedron Lett. 1964, 5, 3879-3886.
36. Karlsson, B.; Pilotti, A.-M.; Söderholm, A.-C.; Norin, T.; Sundin S.; Sumimoto, M. Tetrahedron 1978, 34, 2349-2354.
37. Begley, M. J.; Jackson, C. B.; Pattenden, G. Tetrahedron 1990, 46, 4907-4924.
38. (a) Koepp, A. E.; Hezari, M.; Zajicek, J.; Vogel, B. S.; Lafever, R. E.; Lewis, N. G.; Croteau, R. J. Biol. Chem. 1995, 270, 8686-8690.
39. (b) Hezari, M.; Lewis, N. G.; Croteau, R. Arch. Biochem. Biophys. 1995, 322, 437-444.
40. (c) Williams, D. C.; Wildung, M. R.; Jin, A. Q.; Dalal, D.; Oliver, J. S.; Coutes, R. M.; Croteau, R. Arch. Biochem. Biophys. 2000, 379, 137-146.
41. Rubenstein, S. M.; Williams, R. M. J. Org. Chem. 1995, 60, 7215-7223.
42. Lin, X.; Hezari, M.; Koepp, A. E.; Floss, H. G.; Croteau, R. Biochemistry 1996, 35, 2968-2977.
43. Williams, D. C.; Carroll, B. J.; Jin, Q.; Rithner, C. D.; Lenger, S. R.; Floss, H. G.; Coates, R. M.; Williams, R. M.; Croteau, R. Chem. Biol. 2000, 7, 969-977.
44. Jin, Q.; Williams, D. C.; Hezari, M.; Croteau, R.; Coates, R. M. J. Org. Chem. Accepted for publication.
45. (a) O'Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645-652.
46. (b) Beguin, C. G. Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; Wiley: Chichester, New York, 1999. pp 601-612.
47. (a) Poulter, C. D.; Rilling, H. C. Acc. Chem. Res. 1978, 11, 307-313.
48. (b) Poulter, C. D.; Rilling, H. C. In Biosynthesis of Isoprenoid Compounds; Porter, J. W.; Spurgeon, S. L., Eds.; J. Wiley: New York, 1981; Vol. 1. pp 193-198.
49. (c) Croteau, R. Arch. Biochem. Biophys. 1986, 251, 777-782.
50. Cane, D. E.; Yang, G.; Xue, Q.; Shim, J.-H. Biochemistry 1995, 34, 2471-2479.
51. (a) Robustell, B.; Abe, I.; Prestwich, G. D. Tetrahedron Lett. 1998, 39, 957-960.
52. (b) Robustell, B.; Abe, I.; Prestwich, G. D. Tetrahedron Lett. 1998, 39, 9385-9388.
53. Machleidt, H.; Wessendorf, R. Liebigs Ann. Chem. 1964, 674, 1-10.
54. Sum, F. W.; Weiler, L. Tetrahedron 1981, 37, 303-317.
55. 5) and 4-benzyloxy-2-methyl-2-butenyl bromide were thwarted by rapid elimination of fluoride from the sulfonyl-stabilized anion to form a phenylsulfonylallene.
56. Komatsu, Y.; Kitazume, T. J. Fluorine Chem. 2000, 102, 61-67.
57. Takai, K.; Heathcock, C. H. J. Org. Chem. 1985, 50, 3247-3251.
58. Poulter, C. D.; Argyle, J. C.; Mash, E. A. J. Biol. Chem. 1978, 253, 7227-7233.
59. Corey, E. J.; Luo, G.; Lin, L.-S. J. Am. Chem. Soc. 1997, 119, 9927-9928.
60. Interestingly, the trans/cis ratio varied with the reaction temperature. Higher selectivity (up to trans/cis. 93:7) was achieved at lower temperature (-78 °C). while ratios of 3:1 to 2:1 were typically obtained at higher temperatures (-45 to 0 °C). Evidently the remote fluoro substituent has a pronounced effect on the stereoeselectivity of the cuprate coupling since Weiler and others reported consistently high stereoselectivity (∼98:2) for similar substrates lacking the fluoro substituent at -43 to 0 °C. (a) Sum, F. W.; Weiler, L. J. Am. Chem. Soc. 1979, 101, 4401-4403.
61. (b) Brown, R. C. D.; Hughes, R. M.; Keily, J.; Kenney, A. Chem. Commun. 2000, 1735-1736.
62. (c) Jin, Y.; Coates, R. M. Org. Synth. Submitted for publication.
63. Collington, E. W.; Meyers, A. I. J. Org. Chem. 1971, 36, 3044-3045.
64. Woodside, A. B.; Huang, Z.; Poulter, C. D. Organic Syntheses: Wiley: New York, 1993; Collect. Vol. VIII. pp 616-620.
65. (a) Hamano, Y.; Kuzuyama, T.; Itoh, N.; Furihata, K.; Seto, H.; Dairi, T. J. Biol. Chem. 2002, 277, 37098-37104.
66. (b) Zini, C. A.; Zanin, K. D.; Christensen, E.; Caramâo, E. B.; Pawliszyn, J. J. Agric. Food Chem. 2003, 51, 2679-2686.
67. (c) Burger, B. V.; Roux, M. L.; Spies, H. S. C.; Truter, V. J. Biosciences 1981, 36, 340-343.
68. Rosen, T.; Taschner, M. J.; Thomas, J. A.; Heathcock, C. H. J. Org. Chem. 1985, 50, 1190-1201.
69. Basar, S.; Koch, A.; Konig, W. A. Flavour Fragrance J. 2001, 16., 315-318.
70. Grenier-Loustalot, M. F.; Lectard, A.; Lichanot, A.; Metras, F. Org. Magn. Reson. 1977, 10, 86-91.
71. Emsley, J. W.; Phillips, L.; Wray, V. Prog. Nucl. Magn. Reson. Spectrosc. 1976, 10, 83-756.
72. (a) Shi, Q.-W.; Oritani, T.; Sugiyama, T. Nat. Prod. Lett. 1999, 13, 81-88.
73. (b) Shi, Q.-W.; Oritani, T.; Sugiyama, T. Planta Med. 1999, 65, 356-359.
74. (c) Duh, C.-Y.; El-Gamal, Ali Ali H.; Wang, S.-K.; Dai, C.-F. J. Nat. Prod. 2002, 65, 1429-1433.
75. (a) Harrison, L. J.; Tori, M.; Taira, Z.; Asakawa, Y. In The 28th Symposium on the Chemistry of Terpenes, Essential Oils, and Aromatics: Kanazawa, Japan. 1984; Chemical Society Japan: Tokyo, Japan, 1984; p 285.
76. (b) Nagashima, F.; Tamada, A.; Fujii, N.; Asakawa, Y. Phytochemistry 1997, 46, 1203-1208.
77. (c) Nagashima, F.; Toyota, M.; Asakawa, Y. Phytochemistry 1990, 29, 2169-2174.
78. (a) Chu, M.; Truumees, I.; Gunnarsson, I.; Bishop, W. R.; Kreutner, W.; Horan, A. C.; Patel, M. G.; Gullo, V. P.; Puar, M. S. J. Antibiot. 1993, 46, 554-563.
79. (b) Tokiwano, T., Fukushi, E.; Endo, T.; Oikawa, H. Chem. Commun. 2004, 1324-1325.
80. (a) Sugano, M.; Sato, A.; Iijima, Y.; Oshima, T.; Furuya, K.; Kuwano, H.; Hata, T.; Hanzawa, H. J. Am. Chem. Soc. 1991, 113, 5463-5464.
81. (b) Susgno, M.; Sato, A.; Iijima, Y.; Furuya, K.; Haruyama, H.; Yoda, K.; Hata, T. J. Org. Chem. 1994, 59, 564-569.
82. Poulter, C. D.; Satterwhite, D. M. Biochemistry 1977, 16, 5470-5478.
83. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 3rd ed.; Harper and Row: New York, 1987; p 144.
84. (a) Johnson, W. S.; Chenera, B.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 493-497.
85. (b) Johnson, W. S.; Fletcher, V. R.; Chenera, B.; Bartlett, W. R.; Tham, F. S.; Kullnig, R. K. J. Am. Chem. Soc. 1993, 115, 497-504.
86. (a) Cane, D. E.; Weiner, S. W. Can. J. Chem. 1994, 72, 118-127.
87. (b) Ravn, M. M.; Coates, R. M.; Jetter, R.; Croteau, R. B. Chem. Commun. 1998, 21-22.
88. (c) Ravn, M. M.; Coates, R. M.; Flory, J. E.; Peters, R. J.; Croteau, R. Org. Lett. 2000, 2, 573-576.
89. 12 are unclear at this time. The probable conformation of the enantiomeric keto diepoxide derivative (C1-C2 and C10-C11 exocyclic bonds axial and equatorial, respectively, as in Figure 6) should have the mobile diepoxy nonane macrocycle in a positive octant, albeit with uncertainty in the exact atomic positions. The anticipated positive contribution from the macrocycle should be offset by the levorotatory effects of the rigid axial and equatorial methyl groups on the cyclohexanone ring. It seems plausible that an anomolaous rotatory contribution might be engendered by a through-space interaction of the n electrons of the 2,3-epoxide with the cyclohexanone carbonyl during the n → π* excitation.