Enantioselective synthesis of natural (-)-austalide B, an unusual ortho ester metabolite produced by toxigenic cultures of Aspergillus ustus

Journal of the American Chemical Society

Volumn 116, Issue 6, 1994, Pages 2665-2666

  Paquette, Leo A ^a   Wang, Ting Zhong ^a   Sivik, Matthew R ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AUSTALIDE B; TERPENOID; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE;

EID: 0028350921     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00085a075     Document Type: Article

References (28)

1. Horak, R.M.; Steyn, P.S.; Van Rooyen, P.H.; Vleggaar, R.; Rabie, C.J. J. Chem. Soc., Chem. Commun. 1981, 126
2. Horak, R.M.; Steyn, P.S.; Vleggaar, R.; Rabie, C.J. J. Chem. Soc., Perkin Trans. 1, 1985, 345.
3. Horak, R.M.; Steyn, P.S.; Vleggaar, R. J. Chem. Soc., Perkin Trans. 1, 1985, 357.
4. Horak, R.M.; Steyn, P.S.; Vleggaar, R.; Rabie, C.J. J. Chem. Soc., Perkin Trans. 1 1985, 363.
5. Dillen, J.L.M.; Horak, R.M.; Maharaj, V.J.; Marais, S.F.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1989, 393
6. de Jesus, A.E.; Horak, R.M.; Steyn, P.S.; Vleggaar, R. J. Chem. Soc., Perkin Trans. 1, 1987, 2253.
7. Bowen, L.; Clifford, K.H.; Phillips, G.T. J. Chem. Soc., Chem. Commun. 1977, 949, 950.
8. Colombo, L.; Gennari, C.; Potenza, D.; Scolastico, C.; Aragozzini, F. J. Chem. Soc., Chem. Commun. 1979, 1021
9. Paquette, L.A.; Schulze, M.M. Heterocycles 1993, 35, 585.
10. Paquette, L.A.; Sivik, M.R. Synth. Commun. 1991, 21, 467.
11. Hajos, Z.; Parrish, D.R. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p 363
12. Bauduin, G.; Pietrasanta, Y. Tetrahedron 1973, 29, 4225.
13. Stork, G.; Rosen, P.; Goldman, N.; Coombs, R.V.; Tsuji, J. J. Am. Chem. Soc. 1965, 87, 275.
14. Smith, H.A.; Huff, B.J.L.; Powers, W.J., III; Caine, D. J. Org. Chem. 1967, 32, 2851.
15. Zoretic, P.A.; Branchaud, B.; Maestrone, T. Tetrahedron Lett. 1975, 527
16. Stork, G.; Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152.
17. Boeckman, R.K., Jr. J. Am. Chem. Soc. 1973, 95, 6867
18. Stork, G.; Jung, M.E. J. Am. Chem. Soc. 1974, 96, 3682
19. Sivik, M.R.; Gallucci, J.C.; Paquette, L.A. J. Org. Chem. 1990, 55, 391
20. Meerwein, H.; Bomer, P.; Fuchs, O.; Sasse, H.J.; Schrodt, H.; Spille, J. Chem. Ber. 1956, 89, 2060
21. Scott, W.J.; Stille, J.K. J. Am. Chem. Soc. 1986, 108, 3033
22. Scott, W.J.; Crisp, G. T.; Stille, J.K. J. Am. Chem. Soc. 1984, 106, 4630
23. Stille, J.K.; Groh, M.L. J. Am. Chem. Soc. 1987, 109, 813
24. Forsyth, C.J.; Clardy, J. J. Am. Chem. Soc. 1988, 110, 5911
25. Chan, C.; Cox, P.B.; Roberts, S.M. J. Chem. Soc., Chem. Cotnmun. 1988, 971
26. Mander, L.N.; Sethi, S.P. Tetrahedron Lett 1983, 24, 5425
27. Farina, V.; Baker, S.R.; Benigni, D.A.; Hauck, S.I.; Sapino, C., Jr. J. Org. Chem. 1990, 55, 5833. rate of deprotection
28. Review: Griffith, W.P.; Ley, S.V. Aldrichimica Acta 1990, 23, 13