title: The enantioselective total synthesis of (+)-clusianone.
abstract: (+)-Clusianone, an exo-type B PPAP with reported anti-HIV and chemoprotective activities, was synthesized in eleven steps with 97% ee starting from acetylacetone. An enantioselective decarboxylative Tsuji-Trost-allylation and a Ru-catalyzed ring-closing metathesis-decarboxylative allylation were used to control both diastereo- and enantioselectivity.
authors.affiliation: Institut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, D-70569 Stuttgart, Germany. bernd.plietker@oc.uni-stuttgart.de.
authors.forename: Fiene
authors.initials: F
authors.lastname: Horeischi
authors.forename: Claudia
authors.initials: C
authors.lastname: Guttroff
authors.forename: Bernd
authors.initials: B
authors.lastname: Plietker
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D001577:Benzophenones / Q000138:chemical synthesis* / Q000737:chemistry; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C118110:7-epiclusianone; D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D001577:Benzophenones; D016227:Benzoquinones; D012428:Ruthenium