title: Synthesis of (±)-7-hydroxylycopodine.
abstract: A six step synthesis of (±)-7-hydroxylycopodine has been achieved in 5% overall yield. In the key step, a Prins cyclization of a bicyclic keto alkyne in 60% H(2)SO(4) forms a tricyclic dihydroxy amino ketone.
authors.affiliation: Department of Chemistry, Brandeis University, Waltham, Massachusetts 02454-9110, USA.
authors.forename: Hong-Yu
authors.initials: HY
authors.lastname: Lin
authors.forename: Barry B
authors.initials: BB
authors.lastname: Snider
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D032501:Huperzia / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C557931:7-hydroxylycopodine; D000470:Alkaloids; D011807:Quinolizines; C513871:clavolonine; C535132:sauroine; C016542:lycopodine