Synthesis of inhibitors of imidazole glycerol phosphate dehydratase

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 5, 1996, Pages 547-552

  Lindell, Stephen D ^a   Earnshaw, Christopher G ^a   Wright, Brian J ^a   Carver, David S ^a   O'Mahony, Mary J ^a   Saville Stones, Elizabeth A ^a  

^a AgrEvo UK Limited   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIAZOLE DERIVATIVE; ENZYME INHIBITOR; HERBICIDE; HYDROLYASE; HYDROLYASE INHIBITOR; IMIDAZOLE GLYCEROL DEHYDRATASE; ORGANOPHOSPHORUS COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; STRUCTURE ACTIVITY RELATION;

EID: 0029930229     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00076-5     Document Type: Article

References (33)

1. This work represents part of an ongoing interest within AgrEvo in using biochemical reasoning to generate leads for the discovery of new agrochemicals. For other recent examples see Baillie, A.C.; Wright, K.; Wright, B.J.; Earnshaw, C.G. Pest. Biochem. Physiol. 1988, 30, 103. Schulz, A.; Spönemann, P.; Köcher, H.; Wengenmayer, F. FEBS Lett., 1988, 238, 375. Lindell, S.D.; Turner, R.M. Tetrahedron Letters 1990, 31, 5381. Baillie, A.C.; Cornell, C.L.; Wright, B.J.; Wright, K. ibid 1992, 33, 5133. Harde, C.; Neff, K.H.; Nordhoff, E.; Gerbling, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett. 1994, 4, 273. Laber, B.; Gerbling, K.P.; Harde, C.; Neff, K.H.; Nordhoff, E.; Pohlenz, H.D. Biochemistry 1994, 33, 3413. Laber, B.; Lindell, S.D.; Pohlenz, H.D. Arch. Microbiol. 1994, 161, 400.
2. This work represents part of an ongoing interest within AgrEvo in using biochemical reasoning to generate leads for the discovery of new agrochemicals. For other recent examples see Baillie, A.C.; Wright, K.; Wright, B.J.; Earnshaw, C.G. Pest. Biochem. Physiol. 1988, 30, 103. Schulz, A.; Spönemann, P.; Köcher, H.; Wengenmayer, F. FEBS Lett., 1988, 238, 375. Lindell, S.D.; Turner, R.M. Tetrahedron Letters 1990, 31, 5381. Baillie, A.C.; Cornell, C.L.; Wright, B.J.; Wright, K. ibid 1992, 33, 5133. Harde, C.; Neff, K.H.; Nordhoff, E.; Gerbling, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett. 1994, 4, 273. Laber, B.; Gerbling, K.P.; Harde, C.; Neff, K.H.; Nordhoff, E.; Pohlenz, H.D. Biochemistry 1994, 33, 3413. Laber, B.; Lindell, S.D.; Pohlenz, H.D. Arch. Microbiol. 1994, 161, 400.
3. This work represents part of an ongoing interest within AgrEvo in using biochemical reasoning to generate leads for the discovery of new agrochemicals. For other recent examples see Baillie, A.C.; Wright, K.; Wright, B.J.; Earnshaw, C.G. Pest. Biochem. Physiol. 1988, 30, 103. Schulz, A.; Spönemann, P.; Köcher, H.; Wengenmayer, F. FEBS Lett., 1988, 238, 375. Lindell, S.D.; Turner, R.M. Tetrahedron Letters 1990, 31, 5381. Baillie, A.C.; Cornell, C.L.; Wright, B.J.; Wright, K. ibid 1992, 33, 5133. Harde, C.; Neff, K.H.; Nordhoff, E.; Gerbling, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett. 1994, 4, 273. Laber, B.; Gerbling, K.P.; Harde, C.; Neff, K.H.; Nordhoff, E.; Pohlenz, H.D. Biochemistry 1994, 33, 3413. Laber, B.; Lindell, S.D.; Pohlenz, H.D. Arch. Microbiol. 1994, 161, 400.
4. This work represents part of an ongoing interest within AgrEvo in using biochemical reasoning to generate leads for the discovery of new agrochemicals. For other recent examples see Baillie, A.C.; Wright, K.; Wright, B.J.; Earnshaw, C.G. Pest. Biochem. Physiol. 1988, 30, 103. Schulz, A.; Spönemann, P.; Köcher, H.; Wengenmayer, F. FEBS Lett., 1988, 238, 375. Lindell, S.D.; Turner, R.M. Tetrahedron Letters 1990, 31, 5381. Baillie, A.C.; Cornell, C.L.; Wright, B.J.; Wright, K. ibid 1992, 33, 5133. Harde, C.; Neff, K.H.; Nordhoff, E.; Gerbling, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett. 1994, 4, 273. Laber, B.; Gerbling, K.P.; Harde, C.; Neff, K.H.; Nordhoff, E.; Pohlenz, H.D. Biochemistry 1994, 33, 3413. Laber, B.; Lindell, S.D.; Pohlenz, H.D. Arch. Microbiol. 1994, 161, 400.
5. This work represents part of an ongoing interest within AgrEvo in using biochemical reasoning to generate leads for the discovery of new agrochemicals. For other recent examples see Baillie, A.C.; Wright, K.; Wright, B.J.; Earnshaw, C.G. Pest. Biochem. Physiol. 1988, 30, 103. Schulz, A.; Spönemann, P.; Köcher, H.; Wengenmayer, F. FEBS Lett., 1988, 238, 375. Lindell, S.D.; Turner, R.M. Tetrahedron Letters 1990, 31, 5381. Baillie, A.C.; Cornell, C.L.; Wright, B.J.; Wright, K. ibid 1992, 33, 5133. Harde, C.; Neff, K.H.; Nordhoff, E.; Gerbling, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett. 1994, 4, 273. Laber, B.; Gerbling, K.P.; Harde, C.; Neff, K.H.; Nordhoff, E.; Pohlenz, H.D. Biochemistry 1994, 33, 3413. Laber, B.; Lindell, S.D.; Pohlenz, H.D. Arch. Microbiol. 1994, 161, 400.
6. This work represents part of an ongoing interest within AgrEvo in using biochemical reasoning to generate leads for the discovery of new agrochemicals. For other recent examples see Baillie, A.C.; Wright, K.; Wright, B.J.; Earnshaw, C.G. Pest. Biochem. Physiol. 1988, 30, 103. Schulz, A.; Spönemann, P.; Köcher, H.; Wengenmayer, F. FEBS Lett., 1988, 238, 375. Lindell, S.D.; Turner, R.M. Tetrahedron Letters 1990, 31, 5381. Baillie, A.C.; Cornell, C.L.; Wright, B.J.; Wright, K. ibid 1992, 33, 5133. Harde, C.; Neff, K.H.; Nordhoff, E.; Gerbling, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett. 1994, 4, 273. Laber, B.; Gerbling, K.P.; Harde, C.; Neff, K.H.; Nordhoff, E.; Pohlenz, H.D. Biochemistry 1994, 33, 3413. Laber, B.; Lindell, S.D.; Pohlenz, H.D. Arch. Microbiol. 1994, 161, 400.
7. This work represents part of an ongoing interest within AgrEvo in using biochemical reasoning to generate leads for the discovery of new agrochemicals. For other recent examples see Baillie, A.C.; Wright, K.; Wright, B.J.; Earnshaw, C.G. Pest. Biochem. Physiol. 1988, 30, 103. Schulz, A.; Spönemann, P.; Köcher, H.; Wengenmayer, F. FEBS Lett., 1988, 238, 375. Lindell, S.D.; Turner, R.M. Tetrahedron Letters 1990, 31, 5381. Baillie, A.C.; Cornell, C.L.; Wright, B.J.; Wright, K. ibid 1992, 33, 5133. Harde, C.; Neff, K.H.; Nordhoff, E.; Gerbling, K.P.; Laber, B.; Pohlenz, H.D. Bioorg. Med. Chem. Lett. 1994, 4, 273. Laber, B.; Gerbling, K.P.; Harde, C.; Neff, K.H.; Nordhoff, E.; Pohlenz, H.D. Biochemistry 1994, 33, 3413. Laber, B.; Lindell, S.D.; Pohlenz, H.D. Arch. Microbiol. 1994, 161, 400.
8. Ray, T.B. in Target Sites of Herbicide Action, Böger, P.; Sandmann, G., Eds.; CRC Press Inc., Boca Raton, Florida, 1989, p 105.
9. The results of our early work were presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. See Pillmoor, J.B.; Lindell, S.D.; Briggs, G.G.; Wright, K. in Eighth International Congress of Pesticide Chemistry : Options 2000, Ragsdale, N.N.; Kearney, P.C.; Plimmer, J.R., Eds. ACS Symposium Series, American Chemical Society, Washington, DC, 1995, p 292. Patent: Wright, B.J.; Lindell, S.D.; Foster, S.G.; Milling, R.J. WO 95/14385, 1995.
10. The results of our early work were presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. See Pillmoor, J.B.; Lindell, S.D.; Briggs, G.G.; Wright, K. in Eighth International Congress of Pesticide Chemistry : Options 2000, Ragsdale, N.N.; Kearney, P.C.; Plimmer, J.R., Eds. ACS Symposium Series, American Chemical Society, Washington, DC, 1995, p 292. Patent: Wright, B.J.; Lindell, S.D.; Foster, S.G.; Milling, R.J. WO 95/14385, 1995.
11. The results of our early work were presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. See Pillmoor, J.B.; Lindell, S.D.; Briggs, G.G.; Wright, K. in Eighth International Congress of Pesticide Chemistry : Options 2000, Ragsdale, N.N.; Kearney, P.C.; Plimmer, J.R., Eds. ACS Symposium Series, American Chemical Society, Washington, DC, 1995, p 292. Patent: Wright, B.J.; Lindell, S.D.; Foster, S.G.; Milling, R.J. WO 95/14385, 1995.
12. Mori, I.; Iwasaki, G.; Matsunaga, S.; Kimura, Y.; Nakano, T.; Hayakawa, K.; Scheidegger, A.; Hatano, M.; Tada, S.; Koizumi, S.; Mano, J.; Ohta, D.; Fonné-Pfister, R. Poster no. 285 presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. Mori, I.; Fonné-Pfister, R.; Matsunaga, S.; Tada, S.; Kimura, Y.; Iwasaki, G.; Mano, J.; Hatano, M.; Nakano, T.; Koizumi, S.; Scheidegger, A.; Hayakawa, K.; Ohta, D. Plant Physiol. 1995, 107, 719. Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunaga, S.; Ogawa, A.; Nakano, T.; Buser, H-P.; Hatano, M.; Tada, S.; Hayakawa, K. J. Am. Chem. Soc. 1995, 117, 4411. Patents: Mori, I.; Iwasaki, G.; Scheidegger, A.; Koizumi, S.; Hayakawa, K.; Mano, J. WO 92/19629, 1992. Hayakawa, K.; Mori, I.; Iwasaki, G.; Matsunaga, S. EP 0,528,760, 1993. Mori, I.; Matsunaga, S.; Kimura, Y. GB 2,271,113, 1994. Ward, E.R.; Volrath, S.; Koizumi, S.; Tada, S.; Mori, I.; Iwasaki, G. WO 94/26909, 1994. Mori, I.; Kimura, Y.; Matsunaga, S.; Nakano, T.; O'Sullivan, A.C. WO 95/18811, 1995.
13. Mori, I.; Iwasaki, G.; Matsunaga, S.; Kimura, Y.; Nakano, T.; Hayakawa, K.; Scheidegger, A.; Hatano, M.; Tada, S.; Koizumi, S.; Mano, J.; Ohta, D.; Fonné-Pfister, R. Poster no. 285 presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. Mori, I.; Fonné-Pfister, R.; Matsunaga, S.; Tada, S.; Kimura, Y.; Iwasaki, G.; Mano, J.; Hatano, M.; Nakano, T.; Koizumi, S.; Scheidegger, A.; Hayakawa, K.; Ohta, D. Plant Physiol. 1995, 107, 719. Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunaga, S.; Ogawa, A.; Nakano, T.; Buser, H-P.; Hatano, M.; Tada, S.; Hayakawa, K. J. Am. Chem. Soc. 1995, 117, 4411. Patents: Mori, I.; Iwasaki, G.; Scheidegger, A.; Koizumi, S.; Hayakawa, K.; Mano, J. WO 92/19629, 1992. Hayakawa, K.; Mori, I.; Iwasaki, G.; Matsunaga, S. EP 0,528,760, 1993. Mori, I.; Matsunaga, S.; Kimura, Y. GB 2,271,113, 1994. Ward, E.R.; Volrath, S.; Koizumi, S.; Tada, S.; Mori, I.; Iwasaki, G. WO 94/26909, 1994. Mori, I.; Kimura, Y.; Matsunaga, S.; Nakano, T.; O'Sullivan, A.C. WO 95/18811, 1995.
14. Mori, I.; Iwasaki, G.; Matsunaga, S.; Kimura, Y.; Nakano, T.; Hayakawa, K.; Scheidegger, A.; Hatano, M.; Tada, S.; Koizumi, S.; Mano, J.; Ohta, D.; Fonné-Pfister, R. Poster no. 285 presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. Mori, I.; Fonné-Pfister, R.; Matsunaga, S.; Tada, S.; Kimura, Y.; Iwasaki, G.; Mano, J.; Hatano, M.; Nakano, T.; Koizumi, S.; Scheidegger, A.; Hayakawa, K.; Ohta, D. Plant Physiol. 1995, 107, 719. Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunaga, S.; Ogawa, A.; Nakano, T.; Buser, H-P.; Hatano, M.; Tada, S.; Hayakawa, K. J. Am. Chem. Soc. 1995, 117, 4411. Patents: Mori, I.; Iwasaki, G.; Scheidegger, A.; Koizumi, S.; Hayakawa, K.; Mano, J. WO 92/19629, 1992. Hayakawa, K.; Mori, I.; Iwasaki, G.; Matsunaga, S. EP 0,528,760, 1993. Mori, I.; Matsunaga, S.; Kimura, Y. GB 2,271,113, 1994. Ward, E.R.; Volrath, S.; Koizumi, S.; Tada, S.; Mori, I.; Iwasaki, G. WO 94/26909, 1994. Mori, I.; Kimura, Y.; Matsunaga, S.; Nakano, T.; O'Sullivan, A.C. WO 95/18811, 1995.
15. Mori, I.; Iwasaki, G.; Matsunaga, S.; Kimura, Y.; Nakano, T.; Hayakawa, K.; Scheidegger, A.; Hatano, M.; Tada, S.; Koizumi, S.; Mano, J.; Ohta, D.; Fonné-Pfister, R. Poster no. 285 presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. Mori, I.; Fonné-Pfister, R.; Matsunaga, S.; Tada, S.; Kimura, Y.; Iwasaki, G.; Mano, J.; Hatano, M.; Nakano, T.; Koizumi, S.; Scheidegger, A.; Hayakawa, K.; Ohta, D. Plant Physiol. 1995, 107, 719. Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunaga, S.; Ogawa, A.; Nakano, T.; Buser, H-P.; Hatano, M.; Tada, S.; Hayakawa, K. J. Am. Chem. Soc. 1995, 117, 4411. Patents: Mori, I.; Iwasaki, G.; Scheidegger, A.; Koizumi, S.; Hayakawa, K.; Mano, J. WO 92/19629, 1992. Hayakawa, K.; Mori, I.; Iwasaki, G.; Matsunaga, S. EP 0,528,760, 1993. Mori, I.; Matsunaga, S.; Kimura, Y. GB 2,271,113, 1994. Ward, E.R.; Volrath, S.; Koizumi, S.; Tada, S.; Mori, I.; Iwasaki, G. WO 94/26909, 1994. Mori, I.; Kimura, Y.; Matsunaga, S.; Nakano, T.; O'Sullivan, A.C. WO 95/18811, 1995.
16. Mori, I.; Iwasaki, G.; Matsunaga, S.; Kimura, Y.; Nakano, T.; Hayakawa, K.; Scheidegger, A.; Hatano, M.; Tada, S.; Koizumi, S.; Mano, J.; Ohta, D.; Fonné-Pfister, R. Poster no. 285 presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. Mori, I.; Fonné-Pfister, R.; Matsunaga, S.; Tada, S.; Kimura, Y.; Iwasaki, G.; Mano, J.; Hatano, M.; Nakano, T.; Koizumi, S.; Scheidegger, A.; Hayakawa, K.; Ohta, D. Plant Physiol. 1995, 107, 719. Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunaga, S.; Ogawa, A.; Nakano, T.; Buser, H-P.; Hatano, M.; Tada, S.; Hayakawa, K. J. Am. Chem. Soc. 1995, 117, 4411. Patents: Mori, I.; Iwasaki, G.; Scheidegger, A.; Koizumi, S.; Hayakawa, K.; Mano, J. WO 92/19629, 1992. Hayakawa, K.; Mori, I.; Iwasaki, G.; Matsunaga, S. EP 0,528,760, 1993. Mori, I.; Matsunaga, S.; Kimura, Y. GB 2,271,113, 1994. Ward, E.R.; Volrath, S.; Koizumi, S.; Tada, S.; Mori, I.; Iwasaki, G. WO 94/26909, 1994. Mori, I.; Kimura, Y.; Matsunaga, S.; Nakano, T.; O'Sullivan, A.C. WO 95/18811, 1995.
17. Mori, I.; Iwasaki, G.; Matsunaga, S.; Kimura, Y.; Nakano, T.; Hayakawa, K.; Scheidegger, A.; Hatano, M.; Tada, S.; Koizumi, S.; Mano, J.; Ohta, D.; Fonné-Pfister, R. Poster no. 285 presented at the Eighth International Congress of Pesticide Chemistry, Washington, DC, 4-9 July, 1994. Mori, I.; Fonné-Pfister, R.; Matsunaga, S.; Tada, S.; Kimura, Y.; Iwasaki, G.; Mano, J.; Hatano, M.; Nakano, T.; Koizumi, S.; Scheidegger, A.; Hayakawa, K.; Ohta, D. Plant Physiol. 1995, 107, 719. Mori, I.; Iwasaki, G.; Kimura, Y.; Matsunaga, S.; Ogawa, A.; Nakano, T.; Buser, H-P.; Hatano, M.; Tada, S.; Hayakawa, K. J. Am. Chem. Soc. 1995, 117, 4411. Patents: Mori, I.; Iwasaki, G.; Scheidegger, A.; Koizumi, S.; Hayakawa, K.; Mano, J. WO 92/19629, 1992. Hayakawa, K.; Mori, I.; Iwasaki, G.; Matsunaga, S. EP 0,528,760, 1993. Mori, I.; Matsunaga, S.; Kimura, Y. GB 2,271,113, 1994. Ward, E.R.; Volrath, S.; Koizumi, S.; Tada, S.; Mori, I.; Iwasaki, G. WO 94/26909, 1994. Mori, I.; Kimura, Y.; Matsunaga, S.; Nakano, T.; O'Sullivan, A.C. WO 95/18811, 1995.
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25. m = 330μM and its concentration was 1mM. The enzyme source was recombinant Saccharomyces cerevisiae IGPD expressed in Escherichia coli.
26. Experimental details describing the preparation of phosphonates 6-10 can be found in our patent. See reference 3.
27. Wiater, A.; Hulanicka, D.; Klopotowski, T. Acta Biochimica Polonica, 1971, 18, 289.
28. Miller, J.M.; Anderson, K.S.; Braccolino, D.S.; Cleary, D.G.; Gruys, K.J.; Han, C.Y.; Lin, K-C.; Pansegrau, P.D.; Ream, J.E.; Sammons, R.D.; Sikorski, J.A. Bioorg. Med. Chem. Lett. 1993, 3, 1435. Miller, M.J.; Braccolino, D.S.; Cleary, D.G.; Ream, J.E.; Walker, M.C.; Sikorski, J.A. ibid. 1994, 4, 2605. Kole, H.K.; Akamatsu, M.; Ye, B.; Yan, X.; Barford, D.; Roller, P.P.; Burke, T.R. Biochem. Biophys. Res. Commun. 1995, 209, 817. Ye, B.; Akamatsu, M.; Shoelson, S.E.; Wolf, G.; Giorgetti- Peraldi, S.; Yan, X.; Roller, P.P.; Burke, T.R. J. Med. Chem. 1995, 38, 4270.
29. Miller, J.M.; Anderson, K.S.; Braccolino, D.S.; Cleary, D.G.; Gruys, K.J.; Han, C.Y.; Lin, K-C.; Pansegrau, P.D.; Ream, J.E.; Sammons, R.D.; Sikorski, J.A. Bioorg. Med. Chem. Lett. 1993, 3, 1435. Miller, M.J.; Braccolino, D.S.; Cleary, D.G.; Ream, J.E.; Walker, M.C.; Sikorski, J.A. ibid. 1994, 4, 2605. Kole, H.K.; Akamatsu, M.; Ye, B.; Yan, X.; Barford, D.; Roller, P.P.; Burke, T.R. Biochem. Biophys. Res. Commun. 1995, 209, 817. Ye, B.; Akamatsu, M.; Shoelson, S.E.; Wolf, G.; Giorgetti- Peraldi, S.; Yan, X.; Roller, P.P.; Burke, T.R. J. Med. Chem. 1995, 38, 4270.
30. Miller, J.M.; Anderson, K.S.; Braccolino, D.S.; Cleary, D.G.; Gruys, K.J.; Han, C.Y.; Lin, K-C.; Pansegrau, P.D.; Ream, J.E.; Sammons, R.D.; Sikorski, J.A. Bioorg. Med. Chem. Lett. 1993, 3, 1435. Miller, M.J.; Braccolino, D.S.; Cleary, D.G.; Ream, J.E.; Walker, M.C.; Sikorski, J.A. ibid. 1994, 4, 2605. Kole, H.K.; Akamatsu, M.; Ye, B.; Yan, X.; Barford, D.; Roller, P.P.; Burke, T.R. Biochem. Biophys. Res. Commun. 1995, 209, 817. Ye, B.; Akamatsu, M.; Shoelson, S.E.; Wolf, G.; Giorgetti- Peraldi, S.; Yan, X.; Roller, P.P.; Burke, T.R. J. Med. Chem. 1995, 38, 4270.
31. Miller, J.M.; Anderson, K.S.; Braccolino, D.S.; Cleary, D.G.; Gruys, K.J.; Han, C.Y.; Lin, K-C.; Pansegrau, P.D.; Ream, J.E.; Sammons, R.D.; Sikorski, J.A. Bioorg. Med. Chem. Lett. 1993, 3, 1435. Miller, M.J.; Braccolino, D.S.; Cleary, D.G.; Ream, J.E.; Walker, M.C.; Sikorski, J.A. ibid. 1994, 4, 2605. Kole, H.K.; Akamatsu, M.; Ye, B.; Yan, X.; Barford, D.; Roller, P.P.; Burke, T.R. Biochem. Biophys. Res. Commun. 1995, 209, 817. Ye, B.; Akamatsu, M.; Shoelson, S.E.; Wolf, G.; Giorgetti-Peraldi, S.; Yan, X.; Roller, P.P.; Burke, T.R. J. Med. Chem. 1995, 38, 4270.
32. The required aldehydes were prepared by alkylation of diethyl malonate with the appropriate haloalkyl acetal (EtONa, EtOH, r.t.) followed by acid hydrolysis (5% aq. HCl, THF, r.t).
33. The required alkenyl ethers were prepared by adapting the methodology described in Chouinard, P.M.; Bartlett, P.A. J. Org. Chem. 1986, 51, 75.