Improved preparation of sulfur substituted 3-vinylpyrrole and its application to the syntheses of chuangxinmycin derivatives.
Sulfur substituted 3-vinylpyrrole 10 was prepared from 3-thio-acetylpyrrole 9 by alkylation with alkyl halide in the presence of propylene oxide. Functionalized 4-alkylthioindoles were made by Diels-Alder reaction of the 3-vinylpyrrole 10 with dienophiles. Chuangxinmycin analogues were synthesized by using some of the functionalized 4-alkylthioindoles as key intermediates.
Yoshida
T
T
Showa Pharmaceutical University, Machida, Tokyo, Japan.
Ito
A
A
Ibusuki
K
K
Murase
M
M
Kotani
E
E
D000215:Acylation; D000478:Alkylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D011758:Pyrroles / Q000737:chemistry*; D013055:Spectrophotometry, Infrared
C446975:3-thioacetylpyrrole; C446974:3-vinylpyrrole; D000900:Anti-Bacterial Agents; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007211:Indoles; D011758:Pyrroles; C014414:chuangxinmycin; C009068:propylene oxide