title: Short, enantioselective total synthesis of chatancin.
abstract: An enantioselective total synthesis of the polycyclic diterpene (+)-chatancin, a potent PAF antagonist, is reported. Proceeding in seven steps from dihydrofarnesal, this synthetic route was designed to circumvent macrocyclization-based strategies to complex, cyclized cembranoids. The described synthesis requires only six chromatographic purifications, is high yielding, and avoids protecting-group manipulations. An X-ray crystal structure of this fragile marine natural product was obtained.
authors.affiliation: Department of Chemistry, University of California, Berkeley, 826 Latimer Hall, Berkeley, CA 94720 (USA).
authors.forename: Yu-Ming
authors.initials: YM
authors.lastname: Zhao
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Maimone
mesh_terms: D000080:Acetals / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D010972:Platelet Activating Factor / Q000037:antagonists & inhibitors / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D000438:Alcohols; D004224:Diterpenes; D005030:Ethylenes; D007659:Ketones; D058116:Lewis Acids; D010972:Platelet Activating Factor; C414662:chatancin; C008223:ketene
keywords: asymmetric synthesis; biomimetic synthesis; cycloaddition reaction; natural products; terpenes