Both enantiomers of chelidonine, a B/C-cis-11-hydroxyhexahydrobenzo [c] phenanthridine alkaloid, were synthesized by manipulation of the B/C-dehydro ring juncture of benzo [c] phenanthridine skeleton using Sharpless asymmetric dihydroxylation and stereospecific catalytic hydrogenation after introduction of oxygen functions on the C ring as key reaction steps for the construction of stereogenic centers.
[Fleming, Matthew J.; McManus, Helen A.; Rudolph, Alena; Chan, Walter H.; Ruiz, Jeremy; Dockendorff, Chris; Lautens, Mark Chemistry - A European Journal, 2008 , vol. 14, # 7 p. 2112 - 2124]