196860-95-4Relevant academic research and scientific papers
Studies on the narciclasine alkaloids: Total synthesis of (+)- narciclasine and (+)-pancratistatin
Rigby, James H.,Maharoof, Umar S. M.,Mateo, Mary E.
, p. 6624 - 6628 (2007/10/03)
Enantioselective total syntheses of the antimmor alkaloids, (+)- narciclasine and (+)-pancratistatin, are reported. These syntheses feature a stereo- and regiocontrolled aryl enamide photocyclization to construct a common, advanced intermediate possessing a transfused BC substructure. Differential functional group interchange in the C-ring of this phenanthridone core structure allows for the production of the two target natural products in enantiomerically pure form.
Design and Enantioselective Synthesis of a Peptidomimetic of the Turn in the Helix-Turn-Helix DNA-Binding Protein Motif
Travins, Jeremy M.,Etzkorn, Felicia A.
, p. 8387 - 8393 (2007/10/03)
A peptidomimetic of the turn in the helix-turn-helix (HTH) motif of DNA-binding proteins was designed and synthesized. Conformational constraint was achieved by an unusual linking of two amino acids with a side chain carbon-carbon bond. A phenyl ring provides the potential for new hydrophobic contacts with the hydrophobic core of the HTH motif. In the mimic, the peptide backbone and the central residue were retained in native form within a 12-membered cyclic tripeptide. The target compound 1b was synthesized by two sequential Horner-Wittig couplings followed by enantioselective hydrogenation with Rh(MeDuPHOS) in eight steps and 35% overall yield. The stereochemical outcome of the key hydrogenation was determined by aromatic ring oxidation with RuO2/NaIO4 to give 2 equiv of Boc-Asp-OMe.
