Condensation of Dimethyl-3-methylglutaconate with Aminoaldehydes : A Diastereoselective Synthesis of 5,6-Dihydro-(2H)-pyran-2-ones

Synlett

Volumn 1997, Issue 2, 1997, Pages 223-224

  Piveteau, Nathalie ^a   Audin, Patrick ^a   Ettouati, Laurent ^a   Paris, Joëlle ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003150105     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-728     Document Type: Article

References (13)

1. Schultz, O.E.; Reimerdes, E.H. Arzneim. Forsch./Drug Res 1973, 23, 776. Alkofahi, A.; Ma, W.; McKenzie, A.T.; Byrn, S.R.; McLaughlin, J.L. J. Nat. Prod. 1989, 52, 1371. Jamieson, D.D.; Duffield A.M. Clin. Exp. Pharmacol. Physiol. 1990, 17, 495. Romines, K.; Morris, J.; Howe, W.J.; Tomich, P.; Horng, M.M.; Chong, K.T.; Hinshaw, R.; Anderson, D.; Strohbach, J.; Turner, S.; Mizsak, S. J. Med. Chem. 1996, 39, 4125.
2. Schultz, O.E.; Reimerdes, E.H. Arzneim. Forsch./Drug Res 1973, 23, 776. Alkofahi, A.; Ma, W.; McKenzie, A.T.; Byrn, S.R.; McLaughlin, J.L. J. Nat. Prod. 1989, 52, 1371. Jamieson, D.D.; Duffield A.M. Clin. Exp. Pharmacol. Physiol. 1990, 17, 495. Romines, K.; Morris, J.; Howe, W.J.; Tomich, P.; Horng, M.M.; Chong, K.T.; Hinshaw, R.; Anderson, D.; Strohbach, J.; Turner, S.; Mizsak, S. J. Med. Chem. 1996, 39, 4125.
3. Schultz, O.E.; Reimerdes, E.H. Arzneim. Forsch./Drug Res 1973, 23, 776. Alkofahi, A.; Ma, W.; McKenzie, A.T.; Byrn, S.R.; McLaughlin, J.L. J. Nat. Prod. 1989, 52, 1371. Jamieson, D.D.; Duffield A.M. Clin. Exp. Pharmacol. Physiol. 1990, 17, 495. Romines, K.; Morris, J.; Howe, W.J.; Tomich, P.; Horng, M.M.; Chong, K.T.; Hinshaw, R.; Anderson, D.; Strohbach, J.; Turner, S.; Mizsak, S. J. Med. Chem. 1996, 39, 4125.
4. Schultz, O.E.; Reimerdes, E.H. Arzneim. Forsch./Drug Res 1973, 23, 776. Alkofahi, A.; Ma, W.; McKenzie, A.T.; Byrn, S.R.; McLaughlin, J.L. J. Nat. Prod. 1989, 52, 1371. Jamieson, D.D.; Duffield A.M. Clin. Exp. Pharmacol. Physiol. 1990, 17, 495. Romines, K.; Morris, J.; Howe, W.J.; Tomich, P.; Horng, M.M.; Chong, K.T.; Hinshaw, R.; Anderson, D.; Strohbach, J.; Turner, S.; Mizsak, S. J. Med. Chem. 1996, 39, 4125.
5. Dussert, A. S.; Audin, P.; Paris, J. Syntett 1993, 507.
6. Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Amer. Chem. Soc., 1984, 106, 5594; Overman, L. E.; Mendelson, L. T.; Jacobsen, E. J. J. Amer. Chem. Soc., 1983, 105, 6629.
7. Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Amer. Chem. Soc., 1984, 106, 5594; Overman, L. E.; Mendelson, L. T.; Jacobsen, E. J. J. Amer. Chem. Soc., 1983, 105, 6629.
8. Reetz, M.T. Angew. Chem. Int. Ed. Engl., 1991, 30, 1531.
9. Garner, P.; Park J. M. J. Org. Chem.; 1987, 52, 2361.
10. Mc Killop, A.; Taylor, R.; Watson, R.; Lewis, N. Synthesis 1994, 31.
11. 4 and concentrated in vacuo to give an oil which was purified by chromatography on silica gel. A mixture of anti and syn racemates 2a (83 / 17) was obtained in 63 % overall yield.
12. 3) (distinct signals) δ 4.67 (dxd, 7 = 8.44 Hz, J′ = 5.33 Hz, 1H).
13. 1H NMR coupling constant (1 Hz) and the molecular modeling study, the preferable conformation of 2a was suggested as such that the dihydropyran ring took pseudo-boat form (Figure 1) with the two hydrogens H5 and H6 in pseudoequatorial position (torsion between H5 and H6 = 65°). The relative stereochemistry at C5 and C6 was based on an analysis of NOEs correlations between H5 and 7-Me and between H5 and H7. The proposed configurations for the main isolated isomer (Table) were established from these NMR data and assuming that the chiral center of the aminoaldehyde was fixed.