Stereoselective synthesis of (+)-aspidofractinine.
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.
Gagnon
David
D
Département de Chimie, Université de Sherbrooke, 2500 Boulevard Université, Sherbrooke, Québec, Canada, J1K 2R1.
Spino
Claude
C
D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D006571:Heterocyclic Compounds; D026121:Indole Alkaloids; C552319:aspidofractinine