Synthesis of functionalized piperidinones

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2432-2436

  Humphries, Mark E ^a   Murphy, James ^a   Phillips, Andrew J ^a   Abell, Andrew D ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

RING-CLOSING METATHESIS;

HYDROGENATION; OXIDATION; STEREOCHEMISTRY;

SYNTHESIS (CHEMICAL);

PIPERIDONE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; DERIVATIZATION; EPOXIDATION; MANNICH REACTION; MOLECULAR INTERACTION; SOLUBILITY; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037459691     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0267091     Document Type: Article

References (18)

1. De Lucca, G. V. Bioorg. Med. Chem. Lett. 1997, 7, 501.
2. (a) Lam, P. Y. S.; Ru, Y.; Jadhav, P. K.; Aldrich, P. E.; De Lucca, G. V.; Eyermann, C. J.; Chang, C.-H.; Emmett, G.; Holler, E. R.; Daneker, W. F.; Li, L.; Confalone, P. N.; McHugh, R. J.; Han, Q.; Markwalder, J. A.; Seitz, S. P.; Sharpe, T. R.; Bacheler, L. T.; Rayner, M. M.; Klabe, R. M.; Shum, L.; Winslow, D. L.; Kornhauser, D. M.; Jackson, D. A.; Erickson-Viitanen, S.; Hodge, C. N. J. Med. Chem. 1996, 39, 3514.
3. (b) Hodge, C. N.; Aldrich, P. E.; Bacheler, L. T.; Chang, C.-H.; Eyermann, C. J.; Garber, S.; Grubb, M.; Jackson, D. A.; Jadhav, P. K.; Korant, B.; Lam, P. Y. S.; Maurin, M. B.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Reid, C.; Sharpe, T. R.; Shum, L.; Winslow, D. L.; Erickson-Viitanen, S. Chem. Biol. 1996, 3, 301.
4. De Lucca, G. V.; Liang, J.; De Lucca, I. J. Med. Chem. 1999, 42, 135.
5. Cohen, J. Science 1996, 272, 1880.
6. Note the use of Schechter-Berger nomenclature [Schechter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157]. The residues on the N-terminal side of the peptide bond that is cleaved are denoted (in order) P1-Pn, and those on the C-terminus are denoted P1′-Pn′. In turn, the corresponding subsites on the enzyme are denoted Sn-Sn′
7. Battistini, L.; Rassu, G.; Pinna, L.; Zanardi F.; Casiraghi, G. Tetrahedron: Asymmetry 1999, 10, 765.
8. Rajendra, G.; Miller, M. J. J. Org. Chem. 1987, 52, 4471.
9. Kaafarani, M.; Crozet, M. P.; Surzur, J.-M. Bull. Chim. Fr. 1981, 2, 449.
10. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974. For a related cyclization, see: Sauriat-Dorizon, H.; and Guibé, F. Tetrahedron. Lett. 1998, 39, 6711.
11. Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974. For a related cyclization, see: Sauriat-Dorizon, H.; and Guibé, F. Tetrahedron. Lett. 1998, 39, 6711
12. Adam, W.; Bialas. J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
13. Reduction is assumed to occur from the face opposite the hydroxyl group. Compare compound 23.
14. Luly, J. R.; Dellaria, J. F.; Plattner, J. J.; Soderquist, J. L.; Yi, N. J. Org. Chem. 1987, 52, 1487.
15. 1H NMR spectra; however, the precursor acyclic amide 17 was observed as a complex mixture of epimers and rotamers.
16. This premise is supported by molecular modeling. A conformational search using Spartan 5.0, for compound 18 (MMF Force Field, Monte Carlo) indicated that all conformers within 5 kcal/mol of the global minimum had the C6 group in a pseudoaxial position and the C3 group pseudoequatorial.
17. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
18. Thompson, W. J.; Fitzgerald, P. M. D.; Holloway, M. K.; Emini, E. A.; Darke, P. L.; McKeever, B. M.; Schleif, W. A.; Quintero, J. C.; Zugay, J. A.; Tucker, T. J.; Schwering, J. E.; Homnick, C. F.; Nunberg, J.; Springer, J. P.; Huff, J. R. J. Med. Chem. 1992, 35, 1685.