Synthesis of (+)-lycoricidine by the application of oxidative and regioselective ring-opening of aziridines.
A highly stereoselective total synthesis of (+)-lycoricidine has been described. The salient features of this synthesis are the one-pot elimination followed by allylation reaction, ring-closing metathesis, stereoselective aziridine formation, Dess-Martin periodinane, and silica gel mediated oxidative ring-opening of aziridine to form alpha,beta-unsaturated ketone (allyl amine) and intramolecular Heck cyclization.
Yadav
J S
JS
Organic Chemistry Division, Indian Institute of Chemical Technology (CSIR), Hyderabad-500 007, India. yadavpub@iict.res.in
Satheesh
G
G
Murthy
Changalvala V S R
CV
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D047151:Amaryllidaceae Alkaloids; D001388:Aziridines; D010617:Phenanthridines; C500283:lycoricidine