Studies of the tandem mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to β-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (-)-Panclicin D

Tetrahedron

Volumn 53, Issue 48, 1997, Pages 16471-16488

  Yang, Hong Woon ^a   Zhao, Cunxiang ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

CHEMICAL REACTION; CONFERENCE PAPER; ENZYME INHIBITION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0001210617     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)01029-6     Document Type: Conference Paper

References (60)

1. For an excellent review in this area, see: a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449.
2. For some recent transformations of β-lactones, see: b) Palomo, c.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201.
3. c) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280.
4. d) Shao, H.; Wang, S. H. H.; Lee, C.-W.; Osapay, G.; Goodman, M. J. Org. Chem. 1995, 60, 2956-2957.
5. e) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950.
6. f) Mead, K. T.; Pillai, S. K. Tetrahedron Lett. 1993, 34, 6997-7000.
7. g) Mead, K. T.; Zemribo, R. Synlett 1996, 1063-1064.
8. h) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066.
9. For some recent examples, see: a) Kozikowski, A. P.; Campiani, G.; Nacci, B.; Sega, A.; Saxena, A.; Doctor, B. P. J. Chem. Soc. Perkin Trans. 1 1996, 1287-1297.
10. b) Corey, E. J.; Reichard, G. A.; Kania, R. Tetrahedron Lett. 1993, 34, 6977-6980.
11. c) White, J. D.; Johnson, A. T. J. Org. Chem. 1994, 59, 3347-3358.
12. For reviews of transformations of epoxides, see: a) Mitsunobu, O. in Comprehensive Org. Synthesis, Vol. 7, Ch. 1.3.4.1, B. M. Trost, Eds., Pergamon Press, New York, 1991.
13. b) Rickborn, B. in Comprehensive Org. Synthesis, Vol. 3, Ch. 3.3, B. M. Trost, Eds., Pergamon Press, New York, 1991.
14. Enantioselective methods: a) Wynberg, H.; Staring, E. G. J. Org. Chem. 1985, 50, 1977-1979.
15. b) Capozzi, G.; Roelens, S.; Talami, S. J. Org. Chem. 1993, 58, 7932-7936.
16. For some recently reported diastereoselective methods, see: c) Arrastia, I.; Lecea, B.; Cossio, F. P. Tetrahedron Lett. 1996, 37, 245-248.
17. d) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201.
18. e) Zemribo, R.; Romo, D. Tetrahedron Lett. 1995, 36, 4159-4162.
19. f) Dirat, O.; Berranger, T.; Langlois, Y. Synlett 1995, 935-937.
20. g) Case-Green, S. C.; Davies, S. G.; Hedgecock, C. J. R. Synlett 1991, 779-780.
21. For excellent reviews on the occurrence and synthesis of β-lactone containing natural products, see: a) Lowe, C.; Vederas, J. Organic Prep. & Proc. Intl. 1995, 27, 305-346.
22. b) Pommier, A.; Pons, J.-M. Synthesis 1995, 729-744.
23. An exception is the elegant Lewis acid catalyzed [2+2] cycloaddition route to the lipstatins recently described: Pommier, A.; Pons, J.-M.; Kocienski, P. J. J. Org. Chem. 1995, 60, 7334-7339 and references cited.
24. For a lead reference, see: Abe, H.; Matsubara, I.; Doi, Y. Macromolecules 1996, 28, 844-853.
25. Leboucher-Durand, M.-A.; Langlois, V.; Guerin, P. Polymer Bulletin 1996, 36, 35-41
26. Yang, H. W.; Romo, D. J. Org. Chem. 1997, 62, 4-5.
27. Hirai, K.; Homma, H.; Mikoshiba, I. Heterocycles 1994, 38, 281-282.
28. (a) Danheiser, R. L.; Nowick, J. S. J. Org. Chem. 1991, 56, 1176-1185.
29. (b) Danheiser, R. L.; Nowick, J. S.; Lee, J. H.; Miller, R. F.; Huboux, A. H. Org. Synth. 1995, 73, 61.
30. Wedler, C.; Kleiner, K.; Kunath, A.; Schick, H. Liebigs. Ann. 1996, 881-885 and references cited.
31. Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. J. Org. Chem. 1996, 61, 8293-8296 and references cited.
32. a) Hirai, K.; Iwano, Y.; Mikoshibba, I.; Koyama, H.; Hishi, T. Heterocycles 1994, 38, 277-280.
33. b) Annunziata, R.; Cinquini, M; Cozzi, F.; Molteni, V.; Schupp, O. Tetrahedron 1996, 52, 2573-2582.
34. c) Suh, K.-H.; Choo, D.-J. Bull. Korean Chem. Soc. 1995, 16, 1003-1006.
35. a) Suh, K.-H.; Choo, D.-J. Tetrahedron Lett. 1995, 36, 6109-6112.
36. b) Suh, K.-H.; Choo, D.-J. Bull. Korean Chem. Soc. 1996, 17, 674-676.
37. Reaction of 4-t-butyldimethylsiloxy butanal led to further reaction of the initially formed β-lactone or an intermediate to give a tetrahydrofuran (ref. 9).
38. In our preliminary report (ref. 9), it was stated that olefinic products were obtained in these reactions, however these were found to be minor products in comparison to the aldol products.
39. Mulzer, J.; Zippel, M.; Bruntrup, G.; Segner, J.; Finke, J. Liebigs Ann. Chem. 1980, 1108.
40. The X-ray data of β-lactone 3o has been deposited with the Cambridge Crystallographic Data Centre.
41. Isolation and biological activity: (a) Yoshinari, K.; Aoki, N.; Ohtsuka, T.; Nakayama, N.; Itezono, Y.; Mutoh, M.; Watanabe, J.; Yokose, K. J. Antibiotics 1994, 47, 1376-1384.
42. Structure determination: (b) Mutoh, M.; Nakada, N.; Matsukuma, S.; Ohshima, S.; Yoshinari, K.; Watanabe, J.; Arisawa, M. J. Antibiotics 1994, 47, 1369-1375.
43. Zhi, J.; Melia, A. T.; Guerciolini, R.; Chung, J.; Kinberg, J.; Hauptman, J. B.; Patel, I. H. Clin. Pharm. Ther. 1994, 56, 82.
44. pc2BAll was prepared by a slightly modified procedure from that reported by: Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401-404. We thank Dr. Tae-Seong Kim for sharing this modified procedure.
45. 2Si β-cyclodextrin column: Shitangkoon, A.; Vigh, G. J. Chromatogr. A 1996, 31-42.
46. Keck, G. E.; Castellino, S. Tet. Lett. 1987, 28, 281-284.
47. Evans, D. A.; Dart, M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996, 118, 4322-4343. We thank an astute referee who pointed out the applicability of Evans' findings to the present reaction.
48. (a) Mukaiyama, T.; Araki, M.; Takei, H. J. Am. Chem. Soc. 1973, 95, 4763-4765.
49. (b) Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. Tetrahedron 1991, 47, 8767-8774.
50. Black, T. H.; Dubay, W. J. I.; Tully, P. S. J. Org. Chem. 1988, 53, 5922-5927.
51. Tamai, Y.; Yoshiwara, H.; Someya, M.; Fukumoto, J.; Miyano, S. J. Chem. Soc., Chem. Commun. 1994, 2281-2282.
52. (a) Kondo, K.; Ryu, Y. Japan. Kokai 72 34,223, 1972; Chem. Abstr. 1973, 78, 29239f
53. (a) Kondo, K.; Ryu, Y. Japan. Kokai 72 34,223, 1972; Chem. Abstr. 1973, 78, 29239f
54. (b) Kondo, K.; Ryu, Y.; Mutsukado, M.; Mochida, K. Japan. Kokai 74,127,922, 1974; Chem. Abstr. 1975, 83, 27855h.
55. (b) Kondo, K.; Ryu, Y.; Mutsukado, M.; Mochida, K. Japan. Kokai 74,127,922, 1974; Chem. Abstr. 1975, 83, 27855h.
56. Case-Green, S. C.; Davies, S. G.; Hedgecock, C. J. R. Synlett 1991, 779-780.
57. McDougal, P. G.; Rico, J. G.; Oh, Y.-I; Condon, B. D. J. Org. Chem. 1986, 51, 3388-3390.
58. (a) Cazes, B.; Verniere, C.; Gore, J. Synth. Commun. 1983, 13, 73-79.
59. (b) Bien, J. T.; Shang, M.; Smith, B. D. J. Org. Chem. 1995, 60, 2147-2152.
60. (c) Costa, A. L.; Piazza, M. G.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001-7002.