Total synthesis of spirotryprostatin B via diastereoselective prenylation.
Spirotryprostatin B was synthesized in eight steps, utilizing an efficient palladium-catalyzed prenylation reaction to construct the quaternary C3 stereocenter. The decarboxylation-alkylation of a series of substituted beta-keto esters is described, demonstrating the broad scope of this class of pronucleophiles and allylating agents.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-0508, USA. bmtrost@stanford.edu
Stiles
Dylan T
DT
D010879:Piperazines / Q000138:chemical synthesis*; D017368:Protein Prenylation; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D010879:Piperazines; D013141:Spiro Compounds; C101781:spirotryprostatin B