1224964-85-5Relevant academic research and scientific papers
A ring contraction strategy toward a diastereoselective total synthesis of (+)-bakkenolide A
Carneiro, Vania M. T.,Ferraz, Helena M. C.,Vieira, Tiago O.,Ishikawa, Eloisa E.,Silva Jr., Luiz F.
supporting information; experimental part, p. 2877 - 2882 (2010/08/13)
A diastereoselective route to (+)-bakkenolide A is presented from the readily available optically active Wieland-Miescher ketone. This novel synthesis of this sesquiterpene lactone features the following as key stereoselective transformations: (i) the ring contraction reaction of a octalone mediated by thallium(III) nitrate (TTN); (ii) a hydrogenation to create the cis-fused junction; and (iii) the formation of the C7 quaternary center through an enolate intermediate. Furthermore, during this work, the absolute configuration of a trinorsesquiterpene isolated from Senecio Humillimus was assigned.
