Asymmetric Synthesis of a Xanthine Dehydrogenase Inhibitor (S)-(–)-BOF-4272 : Mechanism of Chiral Diaryl Sulfoxide Formation

REFERENCES AND NOTES

• Sato , S. , Tatsumi , K. and Nishino , T. 1991 . Purine and Pyrimidine Metabolism in Man , Edited by: Harkness , R. A. Vol. VII , 135 New York : Plenum Press . b M Nishimura K Yamaoka H Yasui S Naito T Nakagawa Biol Pharm Bull 17 18 Biochem Pharmacol 46 2277 1993
   Google Scholar
• Prous J. Graul A. Castaner J. , Drug of the Future , 18 , 791 ( 1993 ).
   Google Scholar
• Fujii S. Kawamura H. Kiyokawa H. Yamada S. , Eur. Pat. Appl. EP 269859 (Cl. C07D487104) , 08. Jun. 1988 , CA 1988, 109, 211092p .
   Google Scholar
• Uematsu T. Nakashima M. , J. Pharmacol. Exp. Ther. , 270 , 453 ( 1994 ).
   PubMed Web of Science ®Google Scholar
• The optical isomers were separated with a preparative HPLC; Iwahara R. Emoto S. Kaga J. Imura Y. Aoki M. Asakawa K. , Iyakuhin Kenkyu , 25 , 426 ( 1994 ).
   Google Scholar
• a) Okamoto K. , Yokohama Igaku , 45 , 47 ( 1994 ); b) K. Okamoto, T. Nishino, J. Biol. Chem. 270, 7816 (1995); K. Okamoto, T. Iwamoto, T. Nishino, Flavins and Flavoproteins, 731 (1993) .
   Google Scholar
• Chu C. K. Watanabe K. A. Fox J. J. , J. Heterocyclic Chem. , 17 , 1435 ( 1980 ).
   Web of Science ®Google Scholar
• a) Walker A. J. , Tetrahedron: Asymmetry , 3 , 961 ( 1992 ); b) N.Komatsu, S. Uemura, J. Org. Synth. Chem. Jpn., 53, 268 (1995); c) H. B. Kagan, Catalytic Asymmetric Synthesis, ed. by I. Ojima, VCH, New York, p203 (1993); d) P. Pitchen, E. Dunach, M. N. Deeshmukh, H. B. Kagan, J. Am. Chem. Soc., 106, 8818 (1984); e) F. A. Davis, S. Chattopadhyay, M. E. Harakal, J. C. Towson, W. H. Watson, I. Tavanaiepour, J. Am. Chem. Soc., 109, 3370 (1987); f) M. Palucki, P. Hanson, E. N. Jacobsen, Tetrahedron Lett., 33, 7111 (1992); g) N. Komatsu, M. Hashizume, T. Sugita, S. Uemura, J. Org. Chem., 58, 4529 (1993); h) K. Noda, N. Hosoya, K. Yanai, R. Irie, T. Katsuki, Tetrahedron Lett., 35, 1887 (1994) .
   Web of Science ®Google Scholar
• a) Andersen K. K. Gaffield W. Papanikolaov N. E. Perkins R. I. , J. Am. Chem. Soc. , 86 , 5637 ( 1964 ); b) F. Rebiere, H. B. Kagan, J. Org. Chem., 56, 5991 (1991); c) D. A. Evans, M. M. Faul, L. Colombo, J. J. Bisaha, J. Clandy, D. J. Cherry, J. Am. Chem. Soc., 114, 5977 (1992); d) I.Fernandes, N. Khiar, J. M. Llera, F. Alcudia, J. Org. Chem., 57, 6789 (1992); e) J. K. Whitesell, M. Wong, J. Org. Chem., 59, 597 (1994) .
   Web of Science ®Google Scholar
• Moriyama M. Yoshimura T. Furukawa N. Numata T. Oae S. , Tetrahedron , 32 , 3003 ( 1976 ).
   Web of Science ®Google Scholar
• Johnson C. R. Bacon C. C. Kingsbury W. D. , Tetrahedron Lett. , 501 ( 1972 ).
   Web of Science ®Google Scholar
• a) Ray D. G. III Koser G. F. , J. Am. Chem. Soc. , 112 , 5672 ( 1990 ); b) T. Kimura, H. Nakayama, N. Furukawa, Heteroatom Chemistry, 7, 199 (1996) .
   Web of Science ®Google Scholar
• Matsugi M. Hashimoto K. Inai M. Fukuda N. Furuta T. Minamikawa J. Otsuka S. , Tetrahedron: Asymmetry , 6 , 2991 ( 1995 ).
   Google Scholar
• Suzuki H. Suematsu M. Ishii H. Kato S. Miki H. Mori M. Ishimura Y. Nishino T. Tsuchiya M. , J. Clin. Invest. , 93 , 155 ( 1994 ).
   PubMed Web of Science ®Google Scholar
• a) Akiba K. Takee K. Shimizu Y. Ohkata K. , J. Am. Chem. Soc. , 108 , 6320 ( 1986 ); b) H. Fujiwara, N. Oi, T. Erata, N. Furukawa, Tetrahedron Lett., 31, 1019 (1990); c) M. M. L. Chen, R. Hoffmann, J. Am. Chem. Soc., 98, 1647 (1976) .
   Web of Science ®Google Scholar
• Preminimizations of models by molecular mechanics (MM) calculation with ESFF force field were conducted in Discover 95.0.0, available from MSI . Semiempirical optimizations and LUMO calculations of models by PM3 were conducted in InsightII/Mopac, available from MSI. Coordinates were transferred to Chem 3D Plus, version 3.1.2, for visualization.
   Google Scholar