Enantioselective preparation of 1-benzyloxy-3-methyl-6-heptene-2,4-diols: Total synthesis of (+)-prelactone C

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4823-4826

  Esumi, Tomoyuki ^a   Fukuyama, Hiroko ^a   Oribe, Reiko ^a   Kawazoe, Kaori ^a   Iwabuchi, Yoshiharu ^a   Irie, Hiroshi ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOISOMERISM;

EID: 0030947378     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01042-3     Document Type: Article

References (29)

1. Cf.: (a) Hanessian, S. The Total Synthesis of Natural Products: The Chiron Approach; Pergamon Press: Oxford, 1983.
2. (b) Hanessian, S. Aldrichimica Acta 1989, 22, 3-15.
3. Hatakeyama, S.; Satoh, K.; Takano, S. Tetrahedron Lett. 1993, 34, 7425-7428.
4. Bindseil, K. U.; Zoeck, A. Helv. Chim. Acta 1993, 76, 150-157.
5. Westley, J. W.; Liu, C.-M.; Seilo, L. H.; Evans, R. H.; Troupe, N.; Blount, J. F.; Chiu, A. M.; Todaro, L. J.; Miller, P. A. J. Antibiot. 1984, 37, 1738-1740.
6. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936-3938.
7. Smith, D. B.; Wang, Z.; Schreiber, S. L. Tetrahedron 1991, 46, 4793-4808.
8. Hatakeyama, S.; Kojima, K.; Fukuyama, H.; Irie, H. Chemistry Lett. 1995, 763-764.
9. For nucleophilic methylations of epoxy alcohols, see: (a) Johnson, M. R.; Nakata, T.; Kishi, Y. Tetrahedron Lett. 1979, 4343-4346.
10. (b) Tius, M. A.; Fauq, A. H. J. Org. Chem. 1983, 48, 4131-4132.
11. (c) Roush, W. R.; Adam, M. A.; Peseckis, S. M. Tetrahedron Lett. 1983, 24, 1377-1380.
12. 1H NMR analysis.
13. Lipshutz, B. H.; Kozlowski, J.; Wilhelm, R. S. J. Am. Chem. Soc. 1982, 104, 2305-2307.
14. 13C NMR, IR, HR MS).
15. 13C NMR 12.7, 39.0, 40.7, 72.8, 73.5, 74.7, 117.9, 127.8, 127.9, 135.0, 137.9.
16. 13C resonances of the acetonide carbons to the empirical rule: Cf.: Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948; Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099-7100.
17. 13C resonances of the acetonide carbons to the empirical rule: Cf.: Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett. 1990, 31, 945-948; Evans, D. A.; Rieger, D. L.; Gage, J. R. Tetrahedron Lett. 1990, 31, 7099-7100.
18. Mitsunobu's method did not give any satisfactory results. Mitsunobu, O. Synthesis 1981, 1-28.
19. The 4-tosyloxy isomer was not detected in this particular case.
20. (a) Kruizinga, W. H.; Strijtveen, B.; Kellogg, R. M. J. Org. Chem. 1981, 46, 4323-4324.
21. (b) Torisawa, Y.; Okabe, H.; Ikegami, S. Chemistry Lett. 1984, 1555-1556.
22. (c) Lerchen, H.-G.; Kunz, H. Tetrahedron Lett. 1985, 26, 5257-5260.
23. (d) Sato, K.; Yoshitomo, A. Chemistry Lett. 1995, 39-40.
24. (e) Shimizu, T.; Hiranuma, S.; Nakata, T. Tetrahedron Lett. 1996, 37, 6145-6148.
25. The inversion reactions of the dimesylates were rather sluggish unlike the reaction of 9 so that the corresponding dienes and trienes were also produced by competitive elimination reactions (< 15%).
26. Usual aqueous work-up led to almost complete hydration of the resulting aldehyde. So the aldehyde was isolated by the following nonaqueous work-up (i. dissolving the reaction mixture into n-hexane; ii. removing the precipitates by suction filtration through Celite; iii. evaporation in vacuo).
27. Okazoe, T.; Takai, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 951-953.
28. Letsinger, R. L.; Kammeyer, C. W. J. Am. Chem. Soc. 1951, 73, 4476.
29. 3 based on Helmchen's method. Cf.: Helmchen, G. Tetrahedron Lett. 1974, 1527.