title: Stereoselective synthesis of (+)-aspidofractinine.
abstract: We describe the synthesis of (+)-aspidofractinine, the enantiomer of a naturally occurring alkaloid of the kopsane family. Key features of the synthesis include a stereospecific cyanate to isocyanate rearrangement on a chiral scaffold, a ring-closing alkene metathesis to cleave the chiral auxiliary, and a chemoselective cyclopropanation to introduce the quaternary carbon at position 7 of aspidofractinine.
authors: Département de Chimie, Université de Sherbrooke, 2500 Boulevard Université, Sherbrooke, Québec, Canada, J1K 2R1.
authors: David
authors: D
authors: Gagnon
authors: Claude
authors: C
authors: Spino
mesh_terms: D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D006571:Heterocyclic Compounds; D026121:Indole Alkaloids; C552319:aspidofractinine