(R)-(+)- and (S)-(−)-5-Ethyl-5-methyl-1,3-dioxolane-2,4-dione Reagents for the Direct Preparation of α-Hydroxy-α-methylbutyrate Esters: Assignment of the Absolute Configuration of the α-Acetoxy-α-methylbutyrate Ester Side Chain of Quassimarin via Total Synthesis

Journal of Organic Chemistry

Volumn 58, Issue 15, 1993, Pages 3789-3790

  Moher, Eric D ^a   Grieco, Paul A ^a   Collins, Jon L ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; 5 ETHYL 5 METHYL 1,3 DIOXOLANE 2,4 DIONE; QUASSIMARIN; QUASSINOID; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER;

EID: 0027179055     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00067a004     Document Type: Article

References (32)

1. J. Stewart and Dagmar K. Riley Graduate Fellow, 1991–1992.
2. Kupchan, S. M.; Streelman, D. R. J. Org. Chem. 1976, 41, 3481.
3. Gaudemer, A.; Polonsky, J. Phytochemistry 1965, 4, 149.
4. Nyburg, S. C.; Walford, G. L.; Yates, P. J. Chem. Soc., Chem. Commun. 1965, 203.
5. For reviews on quassinoids see: Kawada, K.; Kim, M.; Watt, D. S. Org. Prep. Proc Int. 1989, 21, 521.
6. Polonsky, J. Fortschr. Chem. Org. Naturst. 1985, 47, 221.
7. Unpublished results with Drs. Thomas H. Corbett and Frederick A. Valeriote, Division of Hematology and Oncology, Wayne State University School of Medicine, Detroit, MI.
8. For model studies on quassimarin and closely related quassinoids, see: Dailey, O. D., Jr.; Fuchs, P. L. J. Org. Chem. 1980, 45, 216.
9. Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175.
10. Kraus, G. A.; Taschner, M.; Shimagaki, M. J. Org. Chem. 1982, 47, 4271.
11. Grieco, P. A.; Sham, H.-L.; Inanaga, J.; Kim, H.; Tuthill, P. A. J. Chem. Soc., Chem. Commun. 1984, 1345.
12. Kanai, K.; Zelle, R. E.; Sham, H.-L.; Grieco, P. A.; Callant, P. J. Org. Chem. 1984, 49, 3867.
13. Batt, D. G.; Takamura, N.; Ganem, B. J. Am. Chem. Soc 1984, 106, 3353.
14. McKittrick, B. A.; Ganem, B. J. Org. Chem. 1985, 50, 5897.
15. Inanaga, J.; Sasaki, S.; Grieco, P. A.; Kim, H. J. Am. Chem. Soc. 1985, 107, 4800.
16. Sasaki, S.; Grieco, P. A.; Huffman, J. C.; Callant, P.; Imamura, P. M. J. Org. Chem. 1985, 50, 4880.
17. Schlessinger, R. H.; Wong, J.; Poss, M. A.; Setoi, H.; Takeno, H.; Hashimoto, M. J. Org. Chem. 1985, 50, 3950.
18. Shishido, K.; Takahashi, K.; Oshio, Y.; Fukumoto, K.; Kametani, T.; Honda, T. Tetrahedron Lett. 1986, 27, 1339.
19. Demir, A.; Gross, R. S.; Dunlap, N. K.; Bashir-Hashemi, A.; Watt, D. S. Tetrahedron Lett. 1986, 27, 5567.
20. Kraus, G. A.; Krolski, M. E. J. Org. Chem. 1986, 51, 3347.
21. Kawabata, T.; Grieco, P. A.; Sham, H.-L.; Kim, H.; Jaw, J. Y.; Tu, S. J. Org. Chem. 1987, 52, 3346.
22. Grieco, P. A.; Inanaga, J.; Sham, H.-L.; Sasaki, S.; Kim, H. J. Chem. Soc., Chem. Commun. 1987, 1044.
23. Spohn, R. F.; Grieco, P. A.; Nargund, R. P. Tetrahedron Lett. 1987, 28, 2491.
24. Shishido, K.; Takahashi, K.; Fukumoto, K.; Kametani, T.; Honda, T. J. Org. Chem. 1987, 52, 5704.
25. Kerwin, S. M.; Paul, A. G.; Heathcock, C. H. J. Org. Chem. 1987, 52, 1686.
26. Kim, M.; Gross, R. S.; Sevestre, H.; Dunlap, N.; Watt, D. S. J. Org. Chem. 1988, 53, 93.
27. Shishido, K.; Takahashi, K.; Oshio, Y.; Fukumoto, K.; Kametani, T.; Honda, T. Heterocycles 1988, 27, 495
28. Kim, M.; Kawada, K.; Gross, R. S.; Watt, D. S. J. Org. Chem. 1990, 55, 504.
29. Mattocks, A. R. J. Chem. Soc 1964, 1918.
30. Hydroxy acids 6 and 7 were prepared according to the protocol of Koga: Jew, S.-S.; Terashima, S.; Koga, K. Tetrahedron 1979, 35, 2337.
31. For the synthesis of 5-substituted 1,3-dioxolane-2,4-diones using trichloromethyl chloroformate see: Toyooka, K.; Takeuchi, Y.; Kubota, S. Heterocycles 1989, 29, 975.
32. Prepared as described previously starting with (R)-(−)-8a-methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione [Moher, E. D.; Collins, J. L.; Grieco, P. A. J. Am. Chem. Soc. 1992, 114, 2764].