NEW APPROACH TO 3-OXYGENATED CARBAZOLES - SYNTHESIS OF HYELLAZOLE AND4-DEOXYCARBAZOMYCIN B

Authors
KAWASAKI T NONAKA Y AKAHANE M MAEDA N SAKAMOTO M
Citation
T. Kawasaki et al., NEW APPROACH TO 3-OXYGENATED CARBAZOLES - SYNTHESIS OF HYELLAZOLE AND4-DEOXYCARBAZOMYCIN B, Journal of the Chemical Society. Perkin transactions. I, (15), 1993, pp. 1777-1781
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
15
Year of publication
1993
Pages
1777 - 1781
Database
ISI
SICI code
0300-922X(1993):15<1777:NAT3C->2.0.ZU;2-8
Abstract
3-Oxygenated carbazoles are prepared in 4 steps from 1-acetyl-2-methox y-1,2-dihydroindol-3-one 6 by Wittig reaction with phosphonium ylides 10 to afford the 3-alkylindoles 11, followed by silylation to the sily l enol ethers 12. Electrocyclic reaction of the enol ethers 12 followe d by desilylation give the 3-hydroxycarbazoles 15. The carbazoles 15a, b were converted into the carbazole alkaloid hyellazole 1 and 4-deoxyc arbazomycin B 2c, respectively.