The intramolecular aldol condensation of 3-oxocyclohexaneacetaldehydes: A useful tool in the synthesis of natural products

Arkivoc

Volumn 2004, Issue 7, 2004, Pages 253-265

  Migneco, Luisa Maria ^a   Leonelli, Francesca ^a   Bettolo, Rinaldo Marini ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

3 oxocyclohexaneacetaldehydes; Intramolecular aldol condensation; Preparation

Indexed keywords

3 OXOCYCLOHEXANEACETALDEHYDE DERIVATIVE; 6 HYDROXYBICYCLO[2.2.2]OCTAN 2 ONE DERIVATIVE; ALDEHYDE DERIVATIVE; KETONE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ALDOL REACTION; CATALYSIS; CHEMICAL REACTION KINETICS; CLAISEN REARRANGEMENT; CYCLIZATION; EPIMER; RACEMIC MIXTURE; REVIEW; SYNTHESIS; THERMODYNAMICS;

EID: 2942659507     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (45)

1. Only 6-hydroxybicyclo[2.2.2]octan-2-ones obtained by intramolecular aldol condensation of a 3-oxocyclohexaneacetaldehyde are taken into account.
2. a) Bell, R. A.; Ireland, R. E. Tetrahedron Lett. 1963, 269.
3. b) Guthrie, R. W.; Philipp, A.; Valenta, Z.; Wiesner, K. ibid. 1965, 2945.
4. c) Guthrie, R. W.; Valenta, Z.; Wiesner, K. ibid. 1966, 4645.
5. d) Bell, R. A.; Ireland, R. E.; Partyka, R. A. J. Am. Chem. Soc. 1966, 31, 2530.
6. e) Mori, K.; Nakahara, Y.; Matsui, M. Tetrahedron 1972, 28, 3217.
7. f) Wiesner, K.; Tsai, T. Y. R.; Huber, K.; Bolton, S. Tetrahedron Lett. 1973, 1233.
8. g) Kelly, R. B.; Eber, J.; Hung, H. K. Can. J. Chem. 1973, 51, 2534.
9. h) Wiesner, K. Pure Appl. Chem. 1975, 41, 93.
10. i) Wiesner, K., Ho, P.; Liu, W.; Shanbhag, M. N. Can. J. Chem. 1975, 53, 2140.
11. j) Tsai, T. Y. R.; Tsai, C. S. J.; Sy, W. W.; Shanbhag, M. N.; Liu, W. C.; Lee, S. F.; Wiesner, K. Heterocycles 1977, 7, 217.
12. k) Kelly, R. B.; Harley, M. L.; Alward, S. J. Can. J. Chem. 1980, 58, 755.
13. l) Bravetti, D.; Marini Bettolo, R.; Lupi, A. Helv. Chim. Acta 1982, 65, 371.
14. m) Kelly, R. B.; Harley, M. L.; Alward, S. J.; Rej, R. N.; Gowda, G.; Mukhopadhyay, A.; Manchand, P.S Can. J. Chem. 1983, 61, 269.
15. n) Marini Bettolo, R.; Tagliatesta, P.; Lupi, A.; Bravetti, D. Helv. Chim. Acta 1983, 66, 760.
16. o) Marini Bettolo, R.; Tagliatesta, P.; Lupi, A.; Bravetti, D. ibid. 1983, 66, 1922.
17. p) Mori, K.; Nagano, E. Biocatalysis 1990, 3, 25.
18. q) Berettoni, M.; Marini Bettolo, R.; Montanari, V.; Prencipe, T.; Romeo, S. Helv. Chim. Acta 1991, 74, 1671.
19. r) Bartoletti, A.; Berettoni, M.; Catteruccia, F.; De Chiara, G.; Marini Bettolo, R.; Mastrangeli, C.; Scarpelli, R.; Tozzi, C.; Lamba, D. Gazz. Chim. Ital. 1996, 126, 223.
20. s) Berettoni, M.; De Chiara, G.; Iacoangeli, T.; Lo Surdo, P.; Marini Bettolo, R.; Montagnini di Mirabello, L.; Nicolini, L.; Scarpelli, R. Helv. Chim. Acta 1996, 79, 2035.
21. Niwa, H.; Hasegawa, T.; Ban, N.; Yamada, K. Tetrahedron 1987, 43, 825.
22. 6-hydroxybicyclo[2.2.2]octan-2-one numbering is used throughout.
23. 2-cyclohexen-1-one numbering is used throughout.
24. As far as stereochemistry of C(6)-OH group in ketols is concerned, in Scheme 2 only the major epimer, if any and when clearly indicated by the Authors, is reported.
25. a) Wiesner, K. Tetrahedron 1975, 31, 1655.
26. b) Marini Bettolo, G.; Sahoo, S.P.; Poulton, C. A.; Tsai, T. Y. R.; Wiesner, K. Tetrahedron 1980, 36, 719.
27. c) Blount, J. F.; Gray, G. D.; Atwal, K. S.; Tsai, T. Y. R.; Wiesner, K. Tetrahedron Lett. 1980, 21, 4413.
28. d) Valenta, K.; Grein, F. Can. J. Chem. 1982, 60, 601.
29. a) ref. 2e;
30. b) Schmoldt, P.; Mattay, J. Synthesis 2003, 7, 1071.
31. Hon, Y.-S.; Chang, F.-J.; Lu, L.; Lin, W.-C. Tetrahedron 1998, 54, 5233.
32. a) Kitahara, T.; Mikaye, M.; Kido, M.; Mori, K. Tetrahedron: Asymmetry 1990, 1, 775.
33. b) Paquette, L. A.; Maleczka, R. E.; Qiu, F. J. Org. Chem. 1991, 56, 2455.
34. The formation, in milder experimental conditions (THF/1N HCl 1.25/1, r. t., 3h) than those usually reported for acid catalyzed intramolecular aldol condensation, of an unsaturated hemiacetal, resulting from the addition of the enolized formyl group to the ketone carbonyl group, has been described.
35. Mori, K.; Matsushima, Y. Synthesis 1993, 406.
36. De Santis, B.; Iamiceli, A. L.; Marini Bettolo, R.; Migneco, L. M.; Scarpelli, R.; Cerichelli, G.; Fabrizi, G.; Lamba, D. Helv. Chim. Acta, 1998, 81, 2375.
37. In a recent work it was pointed out that 6-exo-hydroxybicyclo[2.2.2]octan-2-one self-assembles in the solid state through intermolecular hydrogen bonds to form a supramolecular helix: Sarvary, I.; Johansson, M. H.; Frejd, T. Cryst. Eng. Comm. 2002, 4(26), 146.
38. Ouellette, R. J.; Booth, G. E. J. Am. Chem. Soc. 1965, 30, 423.
39. A referee is pointing out that the 0.6 kcal/mol energy difference between theendo and the exo isomer corresponds to the A value for the OH group.
40. E. L. Eliel, S.H. Wilen, L.N. Mander, Stereochemistry of Organic Compounds, John Wiley & Sons, Inc., New York 1994, p. 695.
41. Under the adopted thioacetalization reaction conditions no epimerization occurs.
42. Marini Bettolo, R.; Migneco, L. M.; Moretti, P.; Scarpelli, R. J. Prakt. Chem. 1999, 341, 687.
43. a) Neverov, A. A.; McDonald, T.; Gibson, G.; Brown, R. S. Can. J. Chem. 2001, 79, 1704.
44. b) Brown, R. S.; Neverov, A. A.J. Chem. Soc., Perkin Trans. 2002, 2, 1039.
45. Di Stefano, S.; Leonelli, F.; Garofalo, B.; Mandolini, L.; Marini Bettolo, R.; Migneco, L. M. Org. Lett. 2002, 4, 2783.