131685-20-6Relevant academic research and scientific papers
Converting cycloalkanones into N-heterocycles: Formal synthesis of (-)-gephyrotoxin 287C
Pichette, Simon,Winter, Dana K.,Lessard, Jean,Spino, Claude
, p. 12532 - 12544 (2014/01/17)
The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When coupled with the Beckmann rearrangement, this photochemical ring contraction converts cycloalkanones into N-heterocycles in a few steps and in a stereospecific manner. To showcase the method, we performed an efficient formal synthesis of (-)-gephyrotoxin 287C.
Uses of aza-cope rearrangement-mannich cyclization reactions to achieve a general entry to melodinus and aspidosperma alkaloids. stereocontrolled total syntheses of (±)-deoxoapodine, (±)-meloscine, and (±)-epimeloscine and a formal synthesis of (±)-1-acetylaspidoalbidine
Overmann, Larry E.,Robertson, Graeme M.,Robichaud, Albert J.
, p. 2598 - 2610 (2007/10/02)
The first total syntheses of the structurally unusual pentacyclic Melodinus alkaloids (±)-meloscine (1) and (±)-epimeloscine (2) and the hexacyclic Aspidosperma alkaloids (±)-deoxoapodine (4) are reported. The syntheses proceed via a highly functionalized common tetracyclic intermediate 7, which is accessed (with complete stereocontrol) by the title rearrangement of pyrindinol 10. These syntheses provide excellent examples of the power of tandem of aza-Cope rearrangement-Mannich cyclization reactions as the key element of stereocontrolled alkaloid synthesis design.
