title: Enantioselective total synthesis of (-)-blennolide A.
abstract: Blennolide A can be synthesized through an enantioselective domino-Wacker/carbonylation/methoxylation reaction of 7a with 96 % ee and an enantioselective Wacker oxidation of 7b with 89 % ee. Further transformations led to the α,β-unsaturated ester (E)-17, which was subjected to a highly selective Michael addition, introducing a methyl group to give 18a. After a threefold oxidation and an intramolecular acylation, the tetrahydroxanthenone 4 was obtained, which could be transformed into (-)-blennolide A (ent-1) in a few steps.
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: Ling
authors: L
authors: Ma
authors: Johannes R
authors: JR
authors: Reiner
authors: Stefan
authors: S
authors: Jackenkroll
authors: Sven
authors: S
authors: Heidemann
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005658:Fungi / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D044004:Xanthones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D044004:Xanthones; C587312:blennolide A; D010165:Palladium