Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.
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.
Perl
Nicholas R
NR
Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.
Ide
Nathan D
ND
Prajapati
Sudeep
S
Perfect
Hahdi H
HH
Durón
Sergio G
SG
Gin
David Y
DY
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
D000480:Alkynes; D002234:Carbodiimides; D007096:Imidoesters; D011743:Pyrimidines; D013141:Spiro Compounds; C507639:crambidine; C012180:2-aminopyrimidine; D019791:Guanidine