188308-51-2Relevant academic research and scientific papers
Asymmetric total synthesis of (+)-virosine A via sequential nucleophilic cyclizations onto an activated formamide
Belanger, Guillaume,Dupuis, Marianne,Larouche-Gauthier, Robin
experimental part, p. 3215 - 3221 (2012/05/19)
The first synthesis of tetracyclic alkaloid virosine A is reported. The natural alkaloid was prepared in only 13 steps, in an enantioenriched form. The azabicyclo[2.2.2]octane core was efficiently assembled using a key Vilsmeier-Haack and Mannich cyclizations sequence performed in one pot.
Asymmetric double ring-opening of a C2h-symmetric bis-epoxide: Improved enantiomeric excess of the product through enantioselective desymmetrisation and 'proof-reading' steps
Ironmonger, Alan,Stockley, Peter,Nelson, Adam
, p. 2350 - 2353 (2007/10/03)
A new strategy in asymmetric synthesis is described in which the desymmetrisation of a C2h-symmetric molecule is followed by a subsequent enantioselective 'proof-reading' step. The double asymmetric ring-opening of the bis-epoxide (1R*, 3R*, 5S
An efficient formal synthesis of balanol via the asymmetric epoxide ring opening reaction
Wu, Michael H.,Jacobsen, Eric N.
, p. 1693 - 1696 (2007/10/03)
An efficient formal synthesis of balanol is described. The thirteen-step sequence features a highly enantioselective (92% ee) ring opening of 1,4-cyclohexadiene monoepoxide with TMSN3 catalyzed by the Cr-salen complex 3. A selective Beckmann rearrangement followed by amide reduction and nitrogen functionalization affords 2, thus completing a formal synthesis of balanol in 31% overall yield.
