Enantioselective synthesis of (+)-juvabione

Journal of Organic Chemistry

Volumn 65, Issue 16, 2000, Pages 5072-5074

  Bergner, Eike J ^a   Helmchen, Günter ^a  

^a UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

JUVENILE HORMONE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

CYCLOHEXANES; JUVENILE HORMONES; STEREOISOMERISM; TREES;

EID: 0034637338     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo005516f     Document Type: Article

References (33)

1. Bowers, W. S.; Fales, H. M.; Thomson, M. J.; Uebel, E. C. Science 1966, 154, 1020-1021.
2. Sláma, K.; Williams, C. M. Proc. Nat. Acad Sci. U.S.A. 1965, 54, 411-414.
3. (a) Manville, J. F.; Bock, K.; von Rudloff, E. Phytochemistry 1977, 16, 1967-1971.
4. (b) Numata, A.; Hokimoto, K.; Takemura, T.; Matsunaga, S.; Morita, R. Chem. Pharm. Bull. 1983, 31, 436-442.
5. Kawai, K.; Takahashi, C.; Miyamoto, T.; Numata, A.; Iwabuchi, H.; Yoshikura, M. Phytochemistry 1993, 32, 331-334.
6. Kawai, K.; Takahashi, C.; Takada, T.; Numata, A. Phytochemistry 1993, 32, 1163-1165.
7. (e) Manville, J. F.; Greguss, L.; Sláma, K.; von Rudloff, E. Collect. Czech. Chem. Commun. 1977, 42, 3658-3666.
8. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Plavac, F.; White, T. C. In Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1983; Vol. 5, p 1.
9. (a) Farges, G.; Veschambre, H. Bull. Soc. Chim. Fr. 1973, 11, 3172-3174.
10. (b) Trost, B. M. Tamaru, Y. J. Am. Chem. Soc. 1977, 99, 3101-3113.
11. Pawson, B. A.; Cheng, H.-C.; Gurbaxani, S.; Saucy, G. J. Am. Chem. Soc. 1977, 99, 336-343.
12. Craveiro, A. A.; Viera, I. G. P. J. Braz. Chem. 1992, 124-126.
13. (e) Fuganti, C.; Serra, S. J. Chem. Soc., Perkin Trans. 1 2000, 97-101.
14. Watanabe, H.; Shimizu, H.; Mori, K. Synthesis 1994, 1249-1254.
15. Miles, W. H.; Brinkman, H. R. Tetrahedron Lett. 1992, 33, 589-592.
16. Nagano, E.; Mori, K. Biosci. Biotech. Biochem. 1992, 56, 1589-1591.
17. Review: Helmchen, G. J. Organomet. Chem. 1999, 576, 203-214.
18. Bergner, E. J.; Helmchen, G. Eur. J. Org. Chem. 2000, 419-423.
19. Bartlett, P. A.; Pizzo, C. F. J. Org. Chem. 1981, 46, 3896-3900.
20. 2 with diastereoselectivity of 96: 4. After flash chromatography epi-3 was obtained in 70% yield with diastereomeric purity >99.99%.
21. (a) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037-3038.
22. (b) Trost, B. M.; Kallander, L. S. J. Org. Chem. 1999, 64, 5427-5435.
23. Bergner, E. J. Diplomarbeit 1997, Universität Heidelberg.
24. Under otherwise equal reaction conditions, the reaction with dimethyl acetoxymalonate (4a) resulted in 50% cleavage of the acetoxy group; at room temperature after a reaction time of 24 h, the substitution product (66%) was still accompanied by the deacetylation product (10%). This side reaction does not occur with ester 4b.
25. Micovic, V. M.; Mihailovic, M. L. J. Org. Chem. 1953, 18, 1190-1200.
26. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
27. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277-7287.
28. Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
29. Grayson, J. I.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1977, 2263-2272.
30. (a) Buss, A. D.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1985, 2307-2325.
31. (b) Zell, R. Helv. Chim. Acta 1979, 62, 474-480.
32. 2O.
33. 1H COSY, HMQC and HMBC experiments.