Practical syntheses of proposed and revised manzacidin B and their congeners.
A concise and highly stereoselective total synthesis of manzacidin B and its congeners has been developed following chelation-controlled syn-epoxidation and Lewis acid catalyzed intramolecular regioselective epoxide ring opening to generate the quarternary amine center. Elaboration of the triol moiety to the target molecule was achieved in good overall yield, representing practical total syntheses of manzacidin B and its congeners. From the XRD, NMR, and analytical data, the correct structure of natural manzacidin B, (4R,5R,6R)-6, was confirmed.
CSIR-National Chemical Laboratory, Pune-411 008, India.
Kuppusamy
K
Sankar
Hasibur
H
Rahman
Pragna P
PP
Das
Eswar
E
Bhimireddy
B
B
Sridhar
Debendra K
DK
Mohapatra
D000588:Amines / Q000737:chemistry; D002384:Catalysis; D004852:Epoxy Compounds / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis*; D011758:Pyrroles / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000588:Amines; D004852:Epoxy Compounds; D011743:Pyrimidines; D011758:Pyrroles; C520151:manzacidin B