Total synthesis of Amaryllidaceae alkaloids utilizing sequential intramolecular heterocyclic azadiene Diels-Alder reactions of an unsymmetrical 1,2,4,5-tetrazine.
Convergent total syntheses of anhydrolycorinone, hippadine, and anhydrolycorinium chloride are detailed, enlisting sequential inverse electron demand Diels-Alder reactions of an unsymmetrical N-acyl-6-amino-1,2,4,5-tetrazine.
Boger
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Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA. boger@scripps.edu
Wolkenberg
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SE
D000470:Alkaloids / Q000138:chemical synthesis*; D047151:Amaryllidaceae Alkaloids; D006571:Heterocyclic Compounds / Q000737:chemistry; D007202:Indicators and Reagents; D010617:Phenanthridines / Q000138:chemical synthesis; D010946:Plants, Medicinal / Q000737:chemistry*
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D006571:Heterocyclic Compounds; D007202:Indicators and Reagents; D010617:Phenanthridines; C420562:anhydrolycorinone; C039688:hippadine