I2–PPh3 mediated spiroannulation of unsaturated b-dicarbonyl compounds. The first synthesis of (±)-negundoin A
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Tapia, Rubén; Cano, M. José; Bouanou, Hanane; Alvarez, Esteban; Alvarez-Manzaneda Roldán, Ramón Jesús; [et al.]Fecha
2013-09-09Resumen
An efficient and stereoselective spiroannulation of unsaturated enols is reported. Unsaturated b-dicarbonyl compounds undergo cyclization by reaction with catalytic I2–PPh3, affording the corresponding spiro enol ether derivatives, with complete regio- and stereoselectivity, under mild conditions. Utilizing this new methodology, the first total synthesis of the anti-inflammatory diterpene negundoin A and a naturally occurring trypanocidal aldehyde is reported.