TiCl4‐Et3N‐mediated one‐step synthesis of γ‐alkylidenebutenolides from ketones: Application to natural product synthesis

TiCl4‐Et3N‐mediated one‐step synthesis of γ‐alkylidenebutenolides from ketones: Application to natural product synthesis

TiCl4‐Et3N‐mediated condensation of ketones with methyl pyruvate afforded γ‐alkylidene butenolides via a tandem cross‐aldol addition/dehydroxylation/intramolecular lactonization process in one‐pot. The application of the methodology to the straightforward synthesis of elem‐1,3,7,8‐tetraen‐8,12‐olide...

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Veröffentlicht in:Journal of heterocyclic chemistry 2020-04, Vol.57 (4), p.2056-2062
Hauptverfasser: Li, Xingyi, Wang, Yanhong, Fu, Kai, Hu, Zhiyong, Li, Zhichun, Ma, Wenbing, Xun, Miao‐Miao, Yuan, Changchun
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes
Alkylidene
Chemistry
Chemistry, Organic
Condensates
Ketones
Natural products
Physical Sciences
Science & Technology
Synthesis
Titanium chlorides
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Zusammenfassung:TiCl4‐Et3N‐mediated condensation of ketones with methyl pyruvate afforded γ‐alkylidene butenolides via a tandem cross‐aldol addition/dehydroxylation/intramolecular lactonization process in one‐pot. The application of the methodology to the straightforward synthesis of elem‐1,3,7,8‐tetraen‐8,12‐olide, chloranthalactone A, and dehydromenthofurolactone, is demonstrated.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3924