119182-74-0Relevant academic research and scientific papers
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.
Total Synthesis of (+/-)-Meloscine and (+/-)-Epimeloscine
Overman, Larry E.,Robertson, Graeme M.,Robichaud, Albert J.
, p. 1236 - 1238 (2007/10/02)
Total syntheses of the Melodinus alkaloids (+/-)-meloscine and (+/-)-epimeloscine are reported.These are the first reported total syntheses of members of this structurally unique alkaloid class.
