2794
J. K. Lynch et al. / Tetrahedron: Asymmetry 9 (1998) 2791–2794
3. Badio, B.; Daly, J. W. Mol. Pharm. 1994, 45, 563–569.
4. Sullivan, J. P.; Decker, M. W.; Brioni, J. D.; Donnelly-Roberts, D.; Anderson, D. J.; Bannon, A. W.; Kang, C.-H.; Adams,
P.; Piattoni-Kaplan, M.; Buckley, M.; Gopalakrishnan, M.; Williams, M.; Arneric, S. P. J. Pharmacol. Exp. Ther. 1994,
271, 624–631.
5. Bonhaus, D. W.; Bley, K. R.; Broka, C. A.; Fontana, D. J.; Leung, E.; Lewis, R.; Shieh, A.; Wong, E. H. F. J. Pharmacol.
Exp. Ther. 1995, 273, 1199–1203.
6. Rao, T. S.; Correa, L. D.; Reid, R. T.; Lloyd, G. K. Neuropharmacology 1996, 35, 393–405.
7. Bannon, A. W.; Decker, M. W.; Holladay, M. W.; Curzon, P.; Donnelly-Roberts, D.; Puttfarcken, P. S.; Bitner, R. S.; Diaz,
A.; Dickenson, A. H.; Porsclt, R. D.; Williams, M.; Arneric, S. P. Science 1998, 279, 77–80.
8. Holladay, M. W.; Wasicak, J. T.; Lin, N.-H.; He, Y.; Ryther, K. B.; Bannon, A. W.; Buckley, M. J.; Kim, D. J. B.; Decker,
M. W.; Anderson, D. J.; Campbell, J. E.; Kuntzweiler, T. A.; Donnelly-Roberts, D. L.; Piattoni-Kaplan, M.; Briggs, C. A.;
Williams, M.; Arneric, S. P. J. Med. Chem. 1998, 41, 407–412.
9. Koch, V.; Schnatterer, S. Synthesis 1990, 499–501.
10. Miyoshi, M.; Sugano, H.; Fujii, T.; Ishihara, T.; Yoneda, N. A. Chem. Lett. 1973, 5–6.
11. Sugano, H.; Miyoshi, M. Bull. Chem. Soc. Jpn 1973, 46, 669–670.
12. Abreo, M. A.; Lin, N.-H.; Garvey, D. S.; Gunn, D. E.; Hettinger, A.-M.; Wasicak, J. T.; Pavlik, P. A.; Martin, Y. C.;
Donnelly-Roberts, D. L.; Anderson, D. J.; Sullivan, J. P.; Williams, M.; Arneric, S. P.; Holladay, M. W. J. Med. Chem.
1996, 39, 817–825.
13. Rodebaugh, R. M.; Cromwell, N. H. J. Heterocycl. Chem. 1969, 6, 435–437.
14. Rodebaugh, R. M.; Cromwell, N. H. J. Heterocycl. Chem. 1969, 6, 993–994.
15. Zervas, L.; Winitz, M.; Greenstein, J. P. J. Org. Chem. 1957, 22, 1515.
16. Salzmann, T. N.; Ratcliffe, R. W.; Christensen, B. G.; Bouffard, F. A. J. Am. Chem. Soc. 1980, 102, 6161–6163.
17. Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Schofield, C. J. Tetrahedron 1990, 46, 4733–4748.
18. Alternatively, removal of the benzyl group of 8 by hydrogenation (Pd/C, 4 atm hydrogen, THF) followed by LAH reduction
produced 4 in 45–55% yield. Although lower yielding, this process eliminated the need for separation of benzyl alcohol
by flash silica gel chromatography.
19. Chiralpak AD column, 90:10 hexane:EtOAc (1.0 mL/min) at 210 nm. Michael Fitzgerald and Michael Rasmussen (D45L)
are gratefully acknowledged for developing the method and running the analyses.
20. Effenberger, F.; Krebs, A.; Willrett, P. Chem. Ber. 1992, 125, 1131–1140.
21. Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; McCollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35,
5409–5412.
22. Dr. Devalina Law of Abbott Laboratories (Pharmaceutics, D4P3) is gratefully acknowledged for evaluation of the physical
properties of the different salts of ABT-594.