Asymmetric, stereocontrolled total synthesis of paraherquamide A.
The first total synthesis of paraherquamide A, a potent anthelmintic agent isolated from various Penicillium sp. with promising activity against drug-resistant intestinal parasites, is reported. Key steps in this asymmetric, stereocontrolled total synthesis include a new enantioselective synthesis of alpha-alkylated-beta-hydroxyproline derivatives to access the substituted proline nucleus and a highly diastereoselective intramolecular S(N)2' cyclization to generate the core bicyclo[2.2.2]diazaoctane ring system.
D000470:Alkaloids / Q000138:chemical synthesis; D000478:Alkylation; D003500:Cyclization; D006909:Hydroxyproline / Q000031:analogs & derivatives / Q000138:chemical synthesis; D026121:Indole Alkaloids; D007211:Indoles / Q000737:chemistry; D007212:Indolizines / Q000138:chemical synthesis*; D010879:Piperazines / Q000138:chemical synthesis; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000470:Alkaloids; D026121:Indole Alkaloids; D007211:Indoles; D007212:Indolizines; D010879:Piperazines; D013141:Spiro Compounds; C007884:gramine; C063985:paraherquamide; D006909:Hydroxyproline