title: Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.
abstract: A convergent synthesis of (-)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.
authors.affiliation: Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
authors.forename: Nicholas R
authors.initials: NR
authors.lastname: Perl
authors.forename: Nathan D
authors.initials: ND
authors.lastname: Ide
authors.forename: Sudeep
authors.initials: S
authors.lastname: Prajapati
authors.forename: Hahdi H
authors.initials: HH
authors.lastname: Perfect
authors.forename: Sergio G
authors.initials: SG
authors.lastname: Durón
authors.forename: David Y
authors.initials: DY
authors.lastname: Gin
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000586:Amination; D002234:Carbodiimides / Q000737:chemistry*; D019791:Guanidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007096:Imidoesters / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D002234:Carbodiimides; D007096:Imidoesters; D011743:Pyrimidines; D013141:Spiro Compounds; C507639:crambidine; C012180:2-aminopyrimidine; D019791:Guanidine