Total synthesis of (-)- and (+)-tedanalactam.
The first stereoselective route providing access to both enantiomers of tedanalactam, a naturally occurring piperidone, has been developed. The stereogenic centers were generated by the use of Sharpless asymmetric dihydroxylation. Tandem oxidation-Wittig reaction and one-pot deprotection, lactamization, and oxirane ring formation are the other key elements.
Majik
Mahesh S
MS
Department of Chemistry, Goa University, Taleigao Plateau, Goa 403 206, India.
Parameswaran
Perunninakulath S
PS
Tilve
Santosh G
SG
D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry; D006900:Hydroxylation; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D007769:Lactams; D010881:Piperidones; C552387:tedanalactam