Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents

Tetrahedron Asymmetry

Volumn 10, Issue 4, 1999, Pages 765-773

  Battistini, Lucia ^a   Rassu, Gloria ^b   Pinna, Luigi ^c   Zanardi, Franca ^a   Casiraghi, Giovanni ^a  

^a Dipto Farmaceutico dell'Univ   (Italy)

^b Ist l'Applic Tecniche Chimiche A   (Italy)

^c UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIBENZYL 5 HYDROXY 6 [(2 PHENYL)ETHYL]PIPERIDIN 2 ONE; GLYCERALDEHYDE; IMINE; LACTAM; PIPERIDONE DERIVATIVE; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG CONFORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033605060     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00051-8     Document Type: Article

References (21)

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10. Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. Engl. 1998, 37, 1044. According to this report, the Lewis acid-promoted imino-aldol coupling of enolate synthons to imines is regarded as a Mannich addition.
11. Remarkable examples: (a) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299; (b) Martin, S. F.; Clark, C. W.; Corbett, J. W J. Org. Chem. 1995, 60, 3236; Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450; (d) Brandstadter, S. M.; Ojima, I., Hirai, K. Tetrahedron Lett. 1987, 28, 613; (e) Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425.
12. Remarkable examples: (a) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299; (b) Martin, S. F.; Clark, C. W.; Corbett, J. W J. Org. Chem. 1995, 60, 3236; Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450; (d) Brandstadter, S. M.; Ojima, I., Hirai, K. Tetrahedron Lett. 1987, 28, 613; (e) Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425.
13. Remarkable examples: (a) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299; (b) Martin, S. F.; Clark, C. W.; Corbett, J. W J. Org. Chem. 1995, 60, 3236; Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450; (d) Brandstadter, S. M.; Ojima, I., Hirai, K. Tetrahedron Lett. 1987, 28, 613; (e) Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425.
14. Remarkable examples: (a) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299; (b) Martin, S. F.; Clark, C. W.; Corbett, J. W J. Org. Chem. 1995, 60, 3236; Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450; Brandstadter, S. M.; Ojima, I., Hirai, K. Tetrahedron Lett. 1987, 28, 613; (e) Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425.
15. Remarkable examples: (a) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299; (b) Martin, S. F.; Clark, C. W.; Corbett, J. W J. Org. Chem. 1995, 60, 3236; Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450; (d) Brandstadter, S. M.; Ojima, I., Hirai, K. Tetrahedron Lett. 1987, 28, 613; (e) Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425.
16. For review articles dealing with the use of heterocyclic silyloxy dienes, including 7, in asymmetric synthesis, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607; (b) Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich; 1998, Vol. 3, p 113.
17. For review articles dealing with the use of heterocyclic silyloxy dienes, including 7, in asymmetric synthesis, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607; (b) Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich; 1998, Vol. 3, p 113.
18. The relative, and hence absolute, configuration of adduct 9 was established based on single-crystal X-ray analysis of a related derivative: Rassu, G.; Pinna, L.; Spanu, P.; Culeddu, N.; Casiraghi, G.; Gasparri Fava, G.; Ferrari Belicchi, M.; Pelosi, G. Tetrahedron 1992, 48, 727.
19. Biological evaluation of target compound 6, as well as constitutional and stereochemical variants will be the subject of future work.
20. Rassu, G.; Zanardi, F.; Battistini, L.; Gaetani, E.; Casiraghi, G. J. Med. Chem. 1997, 40, 168.
21. Schmid, C. R.; Bryant, J. D. Org. Synth. 1995, 72, 6.