title: Total synthesis of norzoanthamine.
abstract: Norzoanthamine, an alkaloid isolated from Zoanthus sp., can suppress the loss of bone weight and strength in ovariectomized mice. Norzoanthamine derivatives can also strongly inhibit the growth of P-388 murine leukemia cell lines and human platelet aggregation. However, norzoanthamine's densely functionalized complex stereostructure and scarce availability from natural sources have proved a synthetic challenge. We report the stereoselective total synthesis of norzoanthamine in 41 steps, with an overall yield of 3.5% (an average of 92% yield each step).
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. miyasita@sci.hokudai.ac.jp
authors.forename: Masaaki
authors.initials: M
authors.lastname: Miyashita
authors.forename: Minoru
authors.initials: M
authors.lastname: Sasaki
authors.forename: Izumi
authors.initials: I
authors.lastname: Hattori
authors.forename: Mio
authors.initials: M
authors.lastname: Sakai
authors.forename: Keiji
authors.initials: K
authors.lastname: Tanino
mesh_terms: D000470:Alkaloids; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006576:Heterocyclic Compounds, 4 or More Rings; D008968:Molecular Conformation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001381:Azepines; D006576:Heterocyclic Compounds, 4 or More Rings; D011804:Quinolines; C400280:norzoanthamine