607405-74-3Relevant academic research and scientific papers
Alkali metal counterion control of enolate protonation stereoselectivity
Hu, Yang,Bishop, Raynauld L.,Luxenburger, Andreas,Dong, Shuzhi,Paquette, Leo A.
, p. 2735 - 2737 (2006)
Generation of the lithium salt of the norbornenol shown (M = H) followed by quenching with aqueous NH4Cl solution gives predominantly the β-epimeric ketone 6. Similar production of the potassium alkoxide leads instead to the α-epimer (99:1). Th
Studies toward the total synthesis of dumsin. 2. A second generation approach resulting in enantioselective construction of a functionalized ABC subunit of the tetranortriterpenoid insect antifeedant
Paquette, Leo A.,Hu, Yang,Luxenburger, Andreas,Bishop, Raynauld L.
, p. 209 - 222 (2007/10/03)
A synthesis of the ABC framework of dumsin is described. The optically active intermediate 9b, which is expeditiously assembled from 5-oxobornyl pivalate by the sequential implementation of an oxy-Cope rearrangement and an intramolecular ene reaction, pro
Total synthesis of dumsin. 1. Retrosynthetic strategy and the elaboration of key intermediates from (-)-bornyl acetate
Paquette, Leo A.,Hong, Fang-Tsao
, p. 6905 - 6918 (2007/10/03)
An intramolecular anionic oxy-Cope rearrangement (44 → 46) serves as the key step in a synthetic approach to the insect antifeedant dumsin. Initial investigations clarified the manner in which (-)-bornyl acetate may be transformed into the exo-norbornenol
