Asymmetric synthesis of α-substituted β-formyl δ-lactones via a Michael addition/α-alkylation protocol

Synlett

Volumn , Issue 5, 1999, Pages 629-631

  Enders, D ^a   Vazquez J ^a  

^a UNIVERSITY HOSPITAL RWTH AACHEN   (Germany)

Author keywords

Alkylation of lactones; Asymmetric synthesis; Formyl anion equivalent; Michael addition; SAMP hydrazone

Indexed keywords

5,6 DIHYDRO 2H PYRAN 2 ONE; BETA FORMYL DELTA LACTONE DERIVATIVE; CYTOSTATIC AGENT; HYDRAZONE DERIVATIVE; LACTONE DERIVATIVE; MACROLIDE; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; OXIDATION; PARTIAL DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TRANS ISOMER;

EID: 0242558731     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2665     Document Type: Article

References (40)

1. For general reviews on lactones see: a) Pielartzik, H.; Irmisch-Pielartzik, B.; Eicher, T. In Houben-Weyl, 4th ed., Vol. E5, part 1; Falbe, J., Ed.; Thieme: Stuttgart 1985; p 715.
2. b) Boyd, G.V. In The Chemistry of Acid Derivatives, The Chemistry of Functional Groups; Patai, S., Ed.; Wiley: Chichester 1979; p 492; 1992; p 548.
3. b) Boyd, G.V. In The Chemistry of Acid Derivatives, The Chemistry of Functional Groups; Patai, S., Ed.; Wiley: Chichester 1979; p 492; 1992; p 548.
4. c) Mulzer, J. In Comprehensive Organic Synthesis, Vol. 6; Trost, B. M.; Fleming, I.; Winterfeldt, E.; Eds.; Pergamon: Oxford 1991; p 323.
5. d) Collins, I. J. Chem. Soc., Perkin Trans. 1 1998, 1869-1888 and references cited therein.
6. Yoshioka, H.; Mabry, T. J.; Timmermann, B. N. Sesquiterpene Lactones; University of Tokyo Press: Tokyo 1973.
7. For reviews see: a) Grieco, P. A. Synthesis 1975, 67.
8. b) Hoffmann, H. M. R.; Rabe, J. Angew. Chem. 1985, 97, 96; Angew. Chem. Int. Ed. Engl. 1985, 24, 94.
9. b) Hoffmann, H. M. R.; Rabe, J. Angew. Chem. 1985, 97, 96; Angew. Chem. Int. Ed. Engl. 1985, 24, 94.
10. c) Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157.
11. d) Sarma, J. C.; Sharma, R. P. Heterocyles 1986, 441.
12. e) Ito, M. Pure Appl. Chem. 1991, 63, 13.
13. For reviews see: a) Nicolaou, K. C. Tetrahedron 1977, 33, 683.
14. b) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem. 1977, 89, 602; Angew. Chem. Int. Ed. Engl 1977, 16, 587.
15. b) Masamune, S.; Bates, G. S.; Corcoran, J. W. Angew. Chem. 1977, 89, 602; Angew. Chem. Int. Ed. Engl 1977, 16, 587.
16. c) Rossa, L.; Vögtle, F. Top. Curr. Chem. 1983, 113, 1.
17. d) Paterson, I.; Mansuri, M. M. Tetrahedron 1985, 41, 3569.
18. e) Boeckmann Jr., R. K.; Goldstein, S. W. In The Total Synthesis of Natural Products, Vol. 7; ApSimon, J., Ed.; Wiley: New York 1988; pl.
19. For alternative asymmetric syntheses of δ-lactones developed in our group see: a) Enders, D.; Rendenbach, B. E. M. Chem. Ber. 1987, 120, 1223.
20. b) Enders, D.; Gröbner, R.; Runsink, J. Synthesis 1995, 947.
21. c) Enders, D.; Kaiser, A. Heterocycles 1997, 46, 631.
22. d) Enders, D.; Teschner, P.; Gröbner, R.; Raabe, G. Synthesis 1999, 237.
23. Enders, D.; Bolkenius, M.; Vázquez, J.; Lassaletta, J. M.; Fernández, R. J. Prakt. Chem. 1998, 340, 281.
24. a) Lassaletta, J. M.; Fernández, R. Tetrahedron Lett. 1992, 33, 3691-3694.
25. b) Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M. Tetrahedron Lett. 1994, 35, 471.
26. c) Enders, D.; Syrig, R.; Raabe, G.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M. Synthesis 1996, 48.
27. d) Lassaletta, J. M.; Fernández, R.; Gasch, C.; Vázquez, J. Tetrahedron 1996, 52, 9143.
28. Lassaletta, J. M.; Fernández, R.; Martín-Zamora, E.; Pareja, C. Tetrahedron Lett. 1996, 37, 5787.
29. a) Lassaletta, J. M.; Fernández, R.; Martín-Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002.
30. b) Díez, E.; Fernández, R.; Gasch, C.; Lassaletta, J. M.; Llera, J. M.; Martín-Zamora, E.; Vázquez, J. J. Org. Chem. 1997, 62, 5144.
31. Fernández, R.; Martín-Zamora, E.; Pareja, C.; Vázquez, J.; Díez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem. 1998, 110, 3598; Angew. Chem. Int. Ed. Engl. 1998, 37, 3428.
32. Fernández, R.; Martín-Zamora, E.; Pareja, C.; Vázquez, J.; Díez, E.; Monge, A.; Lassaletta, J. M. Angew. Chem. 1998, 110, 3598; Angew. Chem. Int. Ed. Engl. 1998, 37, 3428.
33. 2O).
34. a) Posner, G. H.; Loomis, G. L. J. Chem. Soc., Chem. Commun. 1972, 892.
35. b) Herrmann, J. L.; Schlessinger, R. H. J Chem. Soc., Chem. Commun. 1973, 711.
36. 2O/pentane).
37. Complete crystallographic details for compounds (R,R)-4b and (R,S)-4c will be published in a full paper in due course.
38. 2O/pentane).
39. a) Hiemstra, H.; Wynberg, H. Tetrahedron Lett. 1977, 2183.
40. b) Enders, D.; Whitehouse, D.L. Synthesis 1996, 621.