771533-73-4Relevant 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.
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.
A general approach toward bakkanes: Short synthesis of (±)- bakkenolide-A (Fukinanolide)
Reddy, D. Srinivasa
, p. 3345 - 3347 (2007/10/03)
(Chemical Equation Presented) An efficient, general, and fully stereocontrolled approach to the family of bakkanes is disclosed. This route highlights a highly diastereoselective Diels-Alder/aldol sequence to furnish the common hydrindane precursor for th
