title: Chemoenzymatic total synthesis of hyperiones A and B.
abstract: The first asymmetric total synthesis of hyperiones A and B, two norlignans from Hypericum chinense, has been accomplished following a chemoenzymatic approach. Key features of this synthesis include the lipase-catalyzed enantioselective desymmetrization of a prochiral allenic diol and a silver-mediated cycloisomerization of the resulting axially chiral product to furnish the furan core structure. Two alternative pathways, a ruthenium-catalyzed redox isomerization on the one side and a platinum-catalyzed hydrogenation on the other, are described to finally obtain the desired norlignans.
authors: Department für Chemie, Universität zu Köln, DE-50939 Cologne, Germany.
authors: Chicco
authors: C
authors: Manzuna Sapu
authors: Jan
authors: J
authors: Deska
mesh_terms: D002384:Catalysis; D006865:Hydrogenation; D020902:Hypericum / Q000737:chemistry*; D017705:Lignans / Q000096:biosynthesis* / Q000138:chemical synthesis* / Q000737:chemistry; D008049:Lipase / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D017705:Lignans; D009942:Organometallic Compounds; C584181:hyperione A; C584182:hyperione B; D008049:Lipase