Synthesis of (4S)-hydroxymethyl-(2R)-(2-propyl)-butyrolactone: A quest for a practical route to an important hydroxyethylene isostere chiron

Tetrahedron

Volumn 53, Issue 18, 1997, Pages 6281-6294

  Hanessian, Stephen ^a   Abad Grillo, Teresa ^a   McNaughton Smith, Grant ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY ANALYSIS;

CHIRON;

EID: 0030901239     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00298-6     Document Type: Article

References (48)

1. For recent pertinent reports, see a) Ager, D.J.; East, M.B. "Asymmetric Synthetic Methodology", CRC Boca Raton, 1996.
2. b) Seyden-Penne, J. "Chiral Auxiliaries and Ligands in Asymmetric Synthesis", J. Wiley & Sons, Inc. New York, N.Y., 1995.
3. c) Sheldon, R.A. Chirotechnology: "Industrial synthesis of Optically Active Compounds", M. Dekker Inc., New York, N.Y., 1993.
4. d) Blaser, H.U. Chem. Rev. 1992, 92, 935.
5. e) Terashima, S. Synlett. 1992, 691.
6. For selected examples, see a) Chakraborty, T.K.; Hussain, K.A.; Thippeswamy, D. Tetrahedron 1995, 51, 3873.
7. b) Boyd, S.A.; Mantei, R.A.; Hsiao, C.; Baker, W.R. J. Org. Chem. 1991, 56, 438.
8. c) Bühlmayer, P.; Caselli, A.; Fuhrer, W.; Göschke, R.; Rasetti, V.; Rüeger, H.; Stanton, J.L.; Criscione, L.; Wood, J.M. J. Med. Chem. 1988, 31, 1839.
9. d) Kemp, D.J. J. Org. Chem. 1986, 51, 3921.
10. e) Rich, D.H. J. Med. Chem. 1985, 28, 264.
11. For a review, see a) Huff, J. R. J. Med. Chem. 1991, 34, 2305.
12. b) Thaisrivongs, S. Annu. Rep. Med. Chem. 1994, 29, 133.
13. a) Greenlee, W.J J. Med. Res. Rev. 1990, 173.
14. b) Boger, J. Trends Pharm. Sci. 1987, 370.
15. c) Ocain, D.; Abou-Gharbia, M. Drugs of the Future 1991, 16, 37.
16. For selected examples, see a) Peyrat, J.-F.; Chaboche, C.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1995, 36, 2757.
17. b) Dorsey, B.D.; Levin, R.B.; McDaniel, S.L.; Vacca, J.P.; Guare, J.P.; Darke, P.L.; Zugay, J.A.; Emmi, E.A.; Schleif, W.A.; Quintero, J.C.; Lin, J.H.; Chen, I.-W.; Holloway, H.K.; Fitzgerald, P.M.D.; Axel, M.G.; Ostovic, D.; Anderson, P.S.; Huff, J.R. J. Med. Chem. 1994, 37, 3445.
18. c) Baker, W.; Pratt, J.K. Tetrahedron 1993,49, 8739.
19. d) Poss, M.A.; Reid, J.A.; Tetrahedron Lett. 1992, 33, 1411.
20. e) Chakravarty, P.K.; de Laszlo, S.E.; Sarnella, C.S.; Springer, J.P.; Schuda, P.F. Tetrahedron Lett. 1989,30, 415.
21. a) Wolf, J.P.; Rapoport, H. J. Org. Chem. 1989,54, 3164.
22. b) Beard, C.D.; Baum, K.; Grakausas, V. J. Org. Chem. 1973, 38, 3673.
23. Rehders, F.; Hoppe, D. Synthesis 1992, 859.
24. Nishi, T.; Kataoka, M.; Morisawa, Y. Chemistry Lett. 1989, 1993.
25. Rouessac, F.P.; Gringore, O.H. Org. Syn. 1984, 63, 121.
26. a) Evans, D.A.; Morrissey, M.M.; Dow, R.L. Tetrahedron Lett. 1985, 26, 6005.
27. b) Evans, D.A.; Morrissey, M.M. J. Am. Chem. Soc. 1984, 106, 3866;
28. Stork, G.; Kahne, D.E. J. Am. Chem. Soc. 1983,105, 1072.
29. Hanessian, S; Pougny, J.-R; Bossenkool, I.K. Tetrahedron 1984, 40, 1289.
30. Tomioka, K.; Cho, Y.-S.; Sato, F.; Koga, K. J. Org. Chem. 1988, 53, 4094.
31. Poss, A.J. and Smyth, M.S. Tetrahedron Lett. 1989, 30, 5201.
32. Studies to try and epimerize the C-2 centre in compound 5 using a variety of bases proved challenging. Only tert-butoxide/THF gave a reasonable ratio (2:5 = 1:1), while other bases including DBU, failed to generate any of the desired isomer. Formation of the lithium enolate (dianion) of 6 followed by protonation with a variety of compounds bearing acidic protons on either oxygen or carbon were unrewarding.
33. See for example a) Hanessian, S.; Faucher, A.-M. J. Org. Chem. 1991, 56, 2947.
34. b) Melillo, D.G.; Liu.T.; Ryan, K.; Stetzinger, M.; Shinkai, I. Tetrahedron Lett. 1981, 22, 913.
35. c) Hughes, D.L. Org. React. 1992, 42, 335.
36. d) Mitsunobu, O. Synthesis 1981, 1.
37. Encouragingly, the amount of C-2 epimer 13 was found to increase when LiOH was employed as the hydroxide source, however, further epimerization experiments using LiOH proved capricious.
38. Millard, A.A.; Rathke, M.W. J. Am. Chem. Soc. 1977, 99, 4833.
39. For the use of α-trimethlysilylketones and aldehydes as alkene precursors, see a) Hudrlik, P.F.; Kulkarni, A.K. J. Am. Chem. Soc. 1981, 103, 6251 and references therein,
40. b) Hudrlik, P.F; Peterson, D. Tetrahedron Lett. 1972, 1785.
41. c) Hudrlik, P.F; Peterson, D. J. Am. Chem. Soc. 1975, 97, 1464.
42. d) Ruden, R.A.; Gaffney, B.L. Synth. Commum. 1975, 5, 15.
43. α-Phenylselenoketones and aldehydes have also been used as similar alkene precursors, see a) Clive, D.L. J.; Russell, C.G. J. Chem. Soc., Chem Commun. 1981, 434.
44. b) Ryu, I.; Murai, S.; Niwa, I.; Sonada, N. Synthesis 1977, 874.
45. For a review see, Ager, D.R. Synthesis 1984, 384.
46. Hauser, C.R.; Hance, C.R. J. Am. Chem. Soc. 1952, 74, 5091.
47. In order to obtain consistently high yields for the cross-aldol step with l -trimethylsilylpropan-2-one, it must be stored at 0 °C and re-distilled prior to use.
48. The use of diethyl ether as the solvent resulted in a 3:1 α:β ratio.