A novel synthesis subtituted naphthalenes

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 893-896

  De Koning, Charles B ^a   Michael, Joseph P ^a   Rousseau, Ainanda L ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; REACTION ANALYSIS;

EID: 0031029034     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02435-5     Document Type: Article

References (21)

1. Thomson, R.H. Naturally Occurring Quinones III: Recent Advances; Chapman and Hall: London and New York, 1987.
2. General reviews: (a) Thomson, R.H. In The Total Synthesis of Natural Products, Vol. 8; ApSimon, J., Ed.; John Wiley & Sons, Inc.: New York, 1992, pp. 311-531
3. (b) Simpson, T.J. In The Chemistry of Natural Products, Thomson, R.H., Ed.; Blackie: Glasgow and London, 1985, pp. 107-153.
4. Some recent examples: (a) Michellamines: Bringmann, G.; Pokorny, F. In The Alkaloids. Chemistry and Pharmacology, Vol. 46; Cordell, G.A., Ed.; Academic Press: San Diego, 1995, Chapter 4, pp. 127-269.
5. (b) Conocurvone: Laatsch, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 422-424.
6. (c) Gossypol: Meyers, A.I.; Willemsen, J.J. Tetrahedron Lett. 1996, 37, 791-792.
7. (d) Bismurrayaquinone A: Bringmann, G.; Ledermann, A.; Stahl, M.; Gulden, K.-P. Tetrahedron 1995, 51, 9353-9360.
8. Reviews on synthesis of biaryls: (a) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem. Int. Ed. Engl. 1990, 29, 977-991.
9. (b) Sainsbury, M. Tetrahedron 1980, 36, 3327-3359.
10. Fanta, P.E. Synthesis 1974, 9-21.
11. Recent examples of the synthesis of atropisomers: (a) Kamikawa, K.; Watanabe, T.; Uemura, M. J. Org. Chem. 1996, 61, 1375-1384.
12. (b) Hobbs, P.D.; Upender, V.; Liu, J.; Pollart, D.J.; Thomas, D.W.; Dawson, M.I. J. Chem. Soc., Chem. Commun. 1996, 923-924.
13. (c) Chau, P.; Czuba, I.R.; Rizzacasa, M.A.; Bringmann, G.; Gulden, K.-P.; Schärfer, M. J. Org. Chem. 1996, 61, 7101-7105.
14. (d) Bringmann, G.; Schupp, O. S. Afr. J. Chem. 1994, 47, 83-102.
15. The synthesis of (1) in 5 steps from 2,4-dimethoxybenzaldehyde will be reported elsewhere.
16. Whitham, G.H. In Comprehensive Organic Chemistry, Vol. 1; Stoddart, J.F., Ed.; Pergamon Press Ltd.: Oxford, 1979, p. 166.
17. +, 20%), 206 (100), 179 (32) and 151 (73).
18. Sibi, M.P.; Dankwardt, J.W.; Snieckus, V. J. Org. Chem. 1986, 51, 271-273.
19. 2, 5-30% ethyl acetate/hexane) to afford the desired products in yields of 33-82%.
20. Sammes, P.G. Tetrahedron 1976, 32, 405-422.
21. Russell, G.A.; Janzen, E.G.; Strom, E.T. J. Am. Chem. Soc. 1964, 86, 1807-1814.