Alkoxyallene-ynes: Selective Preparation of Bicyclo[5.3.0] Ring Systems Including a δ-Alkoxy Cyclopentadienone
Aurélien Tap1, Camille Lecourt1, Sabrina Dhambri1
1Faculté des Sciences Pharmaceutiques et Biologiques, Unité CNRS UMR 8638 COMÈTE, Paris Descartes University, Sorbonne Paris Cité, 4 avenue de l'observatoire, 75270, Paris cedex 06, France.
Abstract:
The development of an intramolecular rhodium(I)-catalyzed Pauson-Khand reaction of alkoxyallene-ynes with a proximal alkoxy group is reported. This reaction, in the presence of a [Rh(cycloocta-1,5-diene)Cl]2/propane-1,3-diylbis(diphenylphosphane) system under a CO atmosphere, constitutes a powerful tool for selectively accessing carbo- and heterobicyclo[5.3.0] frameworks featuring an enol ether moiety. Through this procedure, a straightforward access to guaiane skeletons with a tertiary hydroxy group at the C10 position was achieved.
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