Search results for "Cryptopleurine"

Synthesis of (-)-Cryptopleurine by Combining Gold(I) Catalysis with a Free Radical Cyclization

2015

(R)-(–)-Cryptopleurine, a highly cytotoxic alkaloid found in Cryptocarya and Boehmeria species, was synthesized in high optical purity using a gold(I)-NHC catalyzed cyclization of an unsymmetrical phenanthrene precursor combined with a free radical cyclization to achieve closure of the C-ring.

Synthesis of (-)-Cryptopleurine by Combining Gold(I) Catalysis with a Free Radical Cyclization (Eur. J. Org. Chem. 10/2015)

2015

Synthesis of alkaloids by Stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methox…

2013

The Stevens rearrangement of nitrile-stabilized ammonium ylides in conjunction with the reductive removal of the nitrile function permits the facile construction of α-branched amines from α-aminonitriles. We employed this reaction sequence for the preparation of (±)-laudanosine, (±)-laudanidine and (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine from two closely related and readily accessible bicyclic α-aminonitriles. The final products were obtained in high to almost quantitative yields (71–98%) from the quaternary ammonium salts obtained by N-alkylation of these starting materials.