Enantioselective construction of biaryl part in the synthesis of stegane related compounds

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2327-2329

  Abe, Hitoshi ^a   Takeda, Shigemitsu ^a   Fujita, Takuro ^a   Nishioka, Keisuke ^a   Takeuchi, Yasuo ^a   Harayama, Takashi ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

Biaryl; Lactone concept; Palladium; Phenyl benzoate; Steganone

Indexed keywords

ANTILEUKEMIC AGENT; BENZOIC ACID DERIVATIVE; BIPHENYL DERIVATIVE; BORANE DERIVATIVE; PALLADIUM; STEGANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 1242315565     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.086     Document Type: Article

References (32)

1. Kupchan S.M., Britton R.W., Ziegler M.F., Gilmore C.J., Restivo B.J., Bryan R.F. J. Am. Chem. Soc. 95:1973;1335-1336.
2. Zavala F., Guenard D., Robin L., Brown E. J. Med. Chem. 23:1980;546-549.
3. Hughes L.R., Raphael R.A. Tetrahedron Lett. 1976;1543-1546.
4. Becker D., Hughes L.R., Raphael R.A. J. Chem. Soc. Perkin. Trans. 1. 1977;1674-1681.
5. Krow G.R., Damodaran K.M., Michener E., Wolf R., Guare J. J. Org. Chem. 43:1978;3950-3953.
6. Mervic M., Ben-David Y., Ghera E. Tetrahedron Lett. 22:1981;5091-5094.
7. Narasimhan N.S., Aidhen I.S. Tetrahedron Lett. 29:1988;2987-2988.
8. Uemura M., Daimon A., Hayashi Y. J. Chem. Soc., Chem. Commun. 1995;1943-1944.
9. Monovich L.G., Le Huérou Y., Rönn M., Molander G.A. J. Am. Chem. Soc. 122:2000;52-57.
10. Kamikawa K., Watanabe T., Daimon A., Uemura M. Tetrahedron. 56:2000;2325-2337.
11. Kende A.S., Liebeskind L.S. J. Am. Chem. Soc. 98:1976;267-268.
12. Magnus P., Schultz J., Gallagher T. J. Chem. Soc., Chem. Commun. 1984;1179-1980.
13. Magnus P., Schultz J., Gallagher T. J. Am. Chem. Soc. 107:1985;4984-4988.
14. Planchenault D., Dhal R., Robin J.P. Tetrahedron. 51:1995;1395-1404.
15. Ward R.S., Hughes D.D. Tetrahedron. 57:2001;2057-2064.
16. Ward R.S., Hughes D.D. Tetrahedron. 57:2001;4015-4022.
17. Meyers A.I., Flisak J.R., Aitken R.A. J. Am. Chem. Soc. 109:1987;5446-5452.
18. Zieglar F.E., Fowler K.W., Sinha N.D. Tetrahedron Lett. 1978;2767-2770.
19. Brown E., Dhal R., Robin J.P. Tetrahedron Lett. 1979;733-736.
20. Larson E.R., Raphael R.A. Tetrahedron Lett. 1979;5041-5042.
21. Ziegler F.E., Chliwner I., Fowler K.W., Kanfer S.J., Kuo S.J., Sinha N.D. J. Am. Chem. Soc. 102:1980;790-798.
22. Robin J.P., Gringore O., Brown E. Tetrahedron Lett. 21:1980;2709-2712.
23. Dhal R., Brown E., Robin J.P. Tetrahedron. 39:1983;2787-2794.
24. Bradley A., Motherwell W.B., Ujjainwalla F. Chem. Commun. 1999;917-918.
25. Bringmann G., Menche D. Acc. Chem. Res. 34:2001;615-624.
26. Bringmann G., Breuning M., Tasler S. Synthesis. 1999;525-558. and references cited therein.
27. 10.
28. Bringmann G., Menche D., Mühlbacher J., Reichert M., Saito N., Pfeiffer S.S., Lipshutz B.H. Org. Lett. 4:2002;2833-2836.
29. Bringmann G., Pabst T., Busemann S. Tetrahedron. 54:1998;1425-1438.
30. Molander G.A., George K.M., Monvich L.G. J. Org. Chem. 68:2003;9533-9540.
31. The Pd-mediated aryl-aryl coupling reaction of phenyl benzoate derivatives has been reported: Harayama T., Yasuda H., Akiyama T., Takeuchi Y., Abe H. Chem. Pharm. Bull. 48:2001;861-864.
32. The ee of 6 was 80% by HPLC analysis.