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

Manabu NODE; Mamoru ARAKI; Hiroaki TANAKA; Daisaku NAKAMURA; Takehisa INOUE; Kiyoharu NISHIDE

doi:10.1248/cpb.46.736

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

Manabu NODE, Mamoru ARAKI, Hiroaki TANAKA, Daisaku NAKAMURA, Takehisa INOUE, Kiyoharu NISHIDE

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Keywords: lipase catalyst, asymmetric synthesis, (-)-isoiridomyrmecin, (+)-loganin aglucon 6-acetate

JOURNAL FREE ACCESS

1998 Volume 46 Issue 4 Pages 736-738

DOI https://doi.org/10.1248/cpb.46.736

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Abstract

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 demethoxy-carbonylation of tetramethyl 3, 7-dioxo-cis-bicyclo-[3.3.0]octane-2, 4, 6, 8-tetracarboxyrate (1).

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