Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P

• Lipase-catalyzed kinetic resolution of γ-cyclogeraniol by Candida antarctica lipase B yielded 23% of optically pure (S)-γ-cyclogeraniol.
• The first synthesis of lufferin-P was achieved.
• The total synthesis of trixagol was achieved.
• The absolute configuration of natural (+)-luffarin-P was determined to have an S configuration.
• The facile synthetic route of β-alkyl-α,β-unsaturated butyrolactone was conducted from alkyl methyl ketone.

Lipase-catalyzed kinetic resolution of γ-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-γ-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-γ-cyclogeraniol, and the absolute configuration of natural (+)-luffarin-P was determined to have an S configuration by our first synthesis of (S)-luffarin-P for the first time.

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