Oxazoline N-oxide-mediated [2 + 3] cycloadditions: Application to a total synthesis of the hypocholesterolemic agent 1233A

Journal of Organic Chemistry

Volumn 63, Issue 19, 1998, Pages 6634-6642

  Dirat, Olivier ^a   Kouklovsky, Cyrille ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYPOCHOLESTEROLEMIC AGENT; PROPIOLACTONE;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION; HYPOCHOLESTEROLEMIA; NONHUMAN;

EID: 0032544469     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980813u     Document Type: Article

References (36)

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6. Total syntheses: (a) Chiang, Y.-C.; Yang, S. S.; Heck, J.; Chabala, J. C.; Chang, M. N. J. Org. Chem. 1989, 54, 570. (b) Mori, K.; Takahashi, Y. Liebigs Ann. Chem. 1991, 1057. (c) Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832. (d) We thank Professor Kocienski for sending us a draft of his paper concerning a new synthesis of 1233A (Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. Submitted for publication). Formal syntheses: (e) Wattanasin, S.; Do, H. D.; Bhongle, N.; Kathawala, F. G. J. Org. Chem. 1993, 58, 1610. (f) Guanti, G.; Banfi, L.; Schmid, G. Tetrahedron Lett. 1994, 35, 4239
7. Total syntheses: (a) Chiang, Y.-C.; Yang, S. S.; Heck, J.; Chabala, J. C.; Chang, M. N. J. Org. Chem. 1989, 54, 570. (b) Mori, K.; Takahashi, Y. Liebigs Ann. Chem. 1991, 1057. (c) Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832. (d) We thank Professor Kocienski for sending us a draft of his paper concerning a new synthesis of 1233A (Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. Submitted for publication). Formal syntheses: (e) Wattanasin, S.; Do, H. D.; Bhongle, N.; Kathawala, F. G. J. Org. Chem. 1993, 58, 1610. (f) Guanti, G.; Banfi, L.; Schmid, G. Tetrahedron Lett. 1994, 35, 4239
8. Total syntheses: (a) Chiang, Y.-C.; Yang, S. S.; Heck, J.; Chabala, J. C.; Chang, M. N. J. Org. Chem. 1989, 54, 570. (b) Mori, K.; Takahashi, Y. Liebigs Ann. Chem. 1991, 1057. (c) Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832. (d) We thank Professor Kocienski for sending us a draft of his paper concerning a new synthesis of 1233A (Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. Submitted for publication). Formal syntheses: (e) Wattanasin, S.; Do, H. D.; Bhongle, N.; Kathawala, F. G. J. Org. Chem. 1993, 58, 1610. (f) Guanti, G.; Banfi, L.; Schmid, G. Tetrahedron Lett. 1994, 35, 4239
9. Total syntheses: (a) Chiang, Y.-C.; Yang, S. S.; Heck, J.; Chabala, J. C.; Chang, M. N. J. Org. Chem. 1989, 54, 570. (b) Mori, K.; Takahashi, Y. Liebigs Ann. Chem. 1991, 1057. (c) Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832. (d) We thank Professor Kocienski for sending us a draft of his paper concerning a new synthesis of 1233A (Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. Submitted for publication). Formal syntheses: (e) Wattanasin, S.; Do, H. D.; Bhongle, N.; Kathawala, F. G. J. Org. Chem. 1993, 58, 1610. (f) Guanti, G.; Banfi, L.; Schmid, G. Tetrahedron Lett. 1994, 35, 4239
10. Total syntheses: (a) Chiang, Y.-C.; Yang, S. S.; Heck, J.; Chabala, J. C.; Chang, M. N. J. Org. Chem. 1989, 54, 570. (b) Mori, K.; Takahashi, Y. Liebigs Ann. Chem. 1991, 1057. (c) Wovkulich, P. M.; Shankaran, K.; Kiegiel, J.; Uskokovic, M. R. J. Org. Chem. 1993, 58, 832. (d) We thank Professor Kocienski for sending us a draft of his paper concerning a new synthesis of 1233A (Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. Submitted for publication). Formal syntheses: (e) Wattanasin, S.; Do, H. D.; Bhongle, N.; Kathawala, F. G. J. Org. Chem. 1993, 58, 1610. (f) Guanti, G.; Banfi, L.; Schmid, G. Tetrahedron Lett. 1994, 35, 4239
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20. Diastereomeric excess was measured at this stage after esterification with methanol, see ref 9.
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24. 4: Chemical equations presented
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26. Iodo alcohol 21 was transformed into the corresponding diiodo derivative. Alkylation of this compound with homoenolate equivalent obtained after deprotonation of tert-butylvinyl ether gave only poor yield of aldehyde 25 (ca. = 20%): Chemical equations presented For alkylation of such homoenolates, see: (a) Still, W. C.; Macdonald, T. L. J. Org. Chem. 1976, 41, 3620. (b) Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560.
27. Iodo alcohol 21 was transformed into the corresponding diiodo derivative. Alkylation of this compound with homoenolate equivalent obtained after deprotonation of tert-butylvinyl ether gave only poor yield of aldehyde 25 (ca. = 20%): Chemical equations presented For alkylation of such homoenolates, see: (a) Still, W. C.; Macdonald, T. L. J. Org. Chem. 1976, 41, 3620. (b) Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560.
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29. Wade, P. A.; Amin, N. V. Synth. Commun. 1982, 12, 287. The temperature of the diimide reduction used in this reaction condition is probably determining.
30. 7.
31. It appeared that protection of primary alcohol was necessary at this stage, since chlorite oxidation as in the model study failed to give the expected acid.
32. Diethyl ether as the solvent gave better yield than dichloromethane because of better solubility.
33. 5 double bond.
34. Adam, W.; Baeza, J.; Ju-Chao, L. J. Am. Chem. Soc. 1972, 94, 2000.
35. Partial retritylation in the presence of trifluoroacetic acid was observed when triphenylmethanol was present in the reaction medium.
36. We thank Dr. C. Jonhstone, Zeneca Pharmaceutical, Macclesfield, U.K., for the generous gift of an authentic sample of 1233A.