New asymmetric syntheses of (-)-isoiridomyrmecin and (+)-loganin aglucon 6-acetate utilizing C2-symmetric dimethyl 3,7-dihydroxy-cis- bicyclo[3.3.0]octa-2,6-diene-2,6-dicarboxylate

Article abstract of DOI:10.1248/cpb.46.736

The first asymmetric synthesis of (-)-isoiridomyrmecin and formal synthesis of (-)-loganin were done using chiral C₂-symmetric building block dimethyl 3,7-dihydroxy-cis-bicyclo[3.3.0]octa-2,6-diene-2,6-dicarboxylate (2) which was prepared by the lipase-catalyzed asymmetric demethoxycarbonylation of tetramethyl 3,7-dioxo-cis-bicyclo-[3.3.0]octane-2,4,6,8-tetracarboxylate (1).

Full text of DOI:10.1248/cpb.46.736

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