Stereoselective synthesis of (+)-avarol, (+)-avarone, and some nonracemic analogues

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8775-8779

  An, Jianguo ^a   Wiemer, David F ^a  

^a University of Iowa   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AVAROL; AVARONE; SESQUITERPENOID;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030443456     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961048r     Document Type: Article

References (24)

1. (1) Faulkner, D. J. Nat. Prod. Rep. 199(5, 13, 75-125, and references cited therein.
2. Minale, L.; Riccio, R.; Sodano, G. Tetrahedron Lett. 1974,3401-3404.
3. deRosa, L.; Minale, L.; Riccio, R.; Sodano, G. J. Chem. Soc., Perkin Trans, l 1976, 1408-1414.
4. Giordano, F.; Puliti, R. Acta Crystallogr. 1987, C43, 985-988.
5. Müller, W. E. G.; Maidhof, A.; Zahn, R. K; Schröder, H. C.; Gasic, M. J.; Heidemann, D.; Bernd, A.; Kurelec, B.; Eich, E.; Seibert, G. Cancer Res. 1985, 45, 4822-4826.
6. (a) Sarin, P. S.; Sun, D.; Thornton, A.; Müller, W. E. G. J. Natl. Cancer Inst. 1987, 78, 663-666.
7. (b) Schröder, H. C.; Sarin, P. S.; Rottmann, M.; Wenger, R.; Maidhof, A.; Renneisen, K.; Müller, W. E. G. Biochem. Pharmacol. 1988, 37, 3947-3952.
8. Kushlan, D. M.; Faulkner, D. J. Tetrahedron 1989, 45, 3307-3312.
9. Rodriguez, J.; Quinoa, E.; Riguera, R.; Peters, B. M.; Abrell, L. M.; Crews, P. Tetrahedron 1992, 48, 6667-6680.
10. Loya, S.; Hizi, A. FEES Lett. 1990, 269, 131-134.
11. (a) Loya, S.; Tal, R.; Kashman, Y.; Hizi, A. Antimicrob. Agents Chemother. 1990, 34, 2009-2112.
12. (b) Loya, S.; Hizi, A. J. Biol. Chem. 1993, 268, 9323-9328.
13. Loya, S.; Tal, R.; Hizi, A.; Issaes, S.; Kashman, Y.; Loya, Y. J. Nat. Prod. 1993, 56, 2120-2125.
14. Sarma, A. S.; Chattopadhyay, P. J. Org. Chem. 1982,47,1727-1731. (corrected 1982, 47, 5427).
15. Watson, A. T.; Park, K.; Wieraer, D. F.; Scott, W. J. J. Org. Chem. 1995, 60, 5102-5106.
16. Bruner, S. D.; Radeke, H. S.; Tallarico, J. A.; Snapper, M. A. J. Org. Chem. 1995, 60, 1114-1115.
17. Yoon, T.; Danishefsky, S. J.; de Gala, S. Angew Chem., Int. Ed. Engl. 1994, 33, 853-855.
18. Uma, R.; Swaminathan, S.; Rajagopalan, K. Tetrahedron Lett. 1984, 25, 5825-5828.
19. Gutzwiller, J.; Buchschacher, P.; Furst, A. Synthesis 1977,167-168.
20. Haghvara, H.; Uda, H. J. Org. Chem. 1988, 53, 2308-2311.
21. Urban, S.; Capon, R. J. Aust. J. Chem. 1994, 47, 1023-1029.
22. An, J.; Wilson, J. M.; An, Y. Z.; Wiemer, D. F. J. Org. Chem. 1996, 61, 4040-4045.
23. (a) MacMurray, J. E. J. Am. Chem. Soc. 1968,90, 6821-6825.
24. (b) Park, K. Ph.D. Thesis, University of Iowa, December, 1993, and references cited therein.