title: Divergent total syntheses of lyconadins A and C.
abstract: Divergent and concise total syntheses of two lycopodium alkaloids, lyconadins A and C have been developed. The synthesis of lyconadin A, having potent neurotrophic activity, features an efficient one-pot ketal removal and formal aza-[4+2] cyclization to form the cagelike core structure. A tandem ketal removal/Mannich reaction was developed to build the tricyclic structure of lyconadin C. Both lyconadins A and C were synthesized from a pivotal intermediate.
authors.affiliation: Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907 (USA) http://www.chem.purdue.edu/dai/
authors.forename: Yang
authors.initials: Y
authors.lastname: Yang
authors.forename: Christopher W
authors.initials: CW
authors.lastname: Haskins
authors.forename: Wandi
authors.initials: W
authors.lastname: Zhang
authors.forename: Pui Leng
authors.initials: PL
authors.lastname: Low
authors.forename: Mingji
authors.initials: M
authors.lastname: Dai
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D055808:Drug Discovery; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001688:Biological Products; D011083:Polycyclic Compounds; C582718:lyconadin C
keywords: alkaloids; cyclizations; drug discovery; natural products; total synthesis