A novel method for the synthesis of phenanthrenes and benzo[a]carbazoles

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8725-8728

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

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

Polycyclic aromatic compounds; Polycyclic heterocyclic compounds; Suzuki reactions

Indexed keywords

CARBAZOLE DERIVATIVE; EPOXIDE; PHENANTHRENE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; IRRADIATION; METHODOLOGY; STEREOCHEMISTRY; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0032547982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01919-4     Document Type: Article

References (23)

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3. 2. (a) Pyrido-fused carbazoles: Gribble, G.W. in The Alkaloids, Vol. 39, Brossi, A. Ed.; Academic Press, Inc., New York, 1990, Chapter 7, pp. 239-343.
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5. (b) Carbazoles: (i) Husson, H.-P. in The Alkaloids, Chemistry and Pharmacology, Vol. 26, Brossi, A., Ed.; Academic Press, Inc., Orlando, 1985, Chapter 1, pp. 1-51. (ii) Chakraborty, D.P. in The Alkaloids, Chemistry and Pharmacology, Vol. 44, Cordell, G.A. Ed.; Academic Press, Inc., San Diego, 1993, Chapter 4, pp. 257-364.
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8. 4. The class of diterpenoid quinones has been reviewed in reference 1(b), Chapter 6, pp. 609-633.
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14. 8. The aromatic bromide (1a) is commercially available. Compound (1b) was prepared by treatment of isovanillin with bromine in acetic acid followed by methylation with dimethyl sulphate in the presence of potassium carbonate and dimethylformamide.
15. 9. (a) Suzuki, A. Acc. Chem. Res. 1982, 15, 178-184.
16. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
17. 2, 5-30% ethyl acetate/hexane) to afford the desired products in yields of 71-99%.
18. 11. All new compounds were characterised spectroscopically and by elemental analysis or high resolution mass spectrometry.
19. 2, 5-30% ethyl acetate/hexane) to afford the desired products in yields of 37-78%.
20. 13. Fu, J.-m.; Sharp, M.J.; Snieckus, V. Tetrahedron Lett. 1988, 29, 5459-5462.
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