485-42-7Relevant articles and documents
Scope and applications of second generation palladium-catalyzed cycloalkenylation. Stereoselective total syntheses of isoiridomyrmecin, isodihydronepetalactone, and α-skytanthine
Takeda, Kazutaka,Toyota, Masahiro
, p. 9909 - 9921 (2012/02/06)
Functionalized bicyclo[3.2.1]octanes, -oxabicyclo-[4.3.0]nonanes, 3-azabicyclo[3.3.0]octanes, and 3-azabicyclo[4.3.0]nonanes were easily synthesized via a second generation palladium-catalyzed cycloalkenylation. Isoiridomyrmecin and isodihydronepetalactone, both of which feature a 3-oxabicyclo[4.3.0]nonane subunit, were stereoselectively synthesized via a second generation palladium-catalyzed cycloalkenylation as the key step. α-Skytanthine, a typical 3-azabicyclo[4.3.0]nonane alkaloid, was also constructed using the same catalytic cyclization protocol.
ENANTIOSELECTIVE SYNTHESES OF (+)-α-SKYTANTHINE, (+)-δ-SKYTANTHINE AND (+)-IRIDOMYRMECIN BY AN INTRAMOLECULAR MAGNESIUM-ENE REACTION.
Oppolzer, Wolfgang,Jacobsen, E. Jon
, p. 1141 - 1144 (2007/10/02)
Starting from (S)-3-methyl-1-penten-5-ol 3a enantiomerically pure (+)-α-skytanthine 9, (+)-δ-skytanthine 11 and (+)-iridomyrmecin 12 were synthesized via the magnesium-ene rection 2*1.