328093-35-2Relevant academic research and scientific papers
Terminating catalytic asymmetric Heck cyclizations by stereoselective intramolecular capture of η3-allylpalladium intermediates: Total synthesis of (-)-spirotryprostatin B and three stereoisomers
Overman, Larry E.,Rosen, Mark D.
experimental part, p. 6514 - 6525 (2010/10/19)
A catalytic intramolecular Heck reaction, followed by capture of the resulting η3-allylpalladium intermediate by a tethered diketopiperazine, is the central step in a concise synthetic route to (-)-spirotryprostatin B and three stereoisomers. This study demonstrates that an acyclic, chiral η3-allylpalladium fragment generated in a catalytic asymmetric Heck cyclization can be trapped by even a weakly nucleophilic diketopiperazine more rapidly than it undergoes diastereomeric equilibration.
Total synthesis of (-)-spirotryprostatin B and three stereoisomers
Overman, Larry E.,Rosen, Mark D.
, p. 4596 - 4599 (2007/10/03)
Heck cyclization and trapping of the resultant η3-allylpalladium intermediate by a tethered diketopiperazine is the central step in a new stereo controlled route to spirotryprostatin alkaloids. The versatility of this approach is illustrated by
