title: Enantioselective total synthesis of (-)-diversonol.
abstract: For the synthesis of (-)-diversonol (ent-1), an enantioselective domino-Wacker/carbonylation/methoxylation reaction and an enantioselective Wacker oxidation were used to give the chroman in high yield and 96% and 93% ee, respectively. Dihydroxylation at the vinyl moiety using the Sharpless procedure and a Wittig-Horner reaction followed by hydrogenation, benzylic oxidation, and an intramolecular acylation provided the tetrahydroxanthenone, from which ent-1 is accessible in a few steps. Furthermore, the synthesis of the diastereomeric diversonol rac-1,9a-epi-diversonol (rac-41) is also described.
authors: Institute of Organic and Biomolecular Chemistry, Georg-August-University Göttingen, Tammannstrasse 2, 37077 Göttingen, Germany. ltietze@gwdg.de
authors: Lutz F
authors: LF
authors: Tietze
authors: Stefan
authors: S
authors: Jackenkroll
authors: Christian
authors: C
authors: Raith
authors: Dirk A
authors: DA
authors: Spiegl
authors: Johannes R
authors: JR
authors: Reiner
authors: Maria Claudia
authors: MC
authors: Ochoa Campos
mesh_terms: D006865:Hydrogenation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D012118:Resorcinols / Q000737:chemistry; D013237:Stereoisomerism; D044004:Xanthones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D012118:Resorcinols; D044004:Xanthones; C514121:diversonol; C005282:orcinol; D010165:Palladium