Synthesis of Polyfunctional Drimanes from Drim-7,9(11)-diene and Drim-8-en-7-one

A series of 15 new polyfunctional drimanic compounds have been obtained by synthesis via dye-sensitized photooxygenation, bromination with N-bromosuccinimide, and electrochemical transformation of drim-7,9(11)-diene 1 and drim-8-en-7-one 2. Three alternative syntheses of 12-acetoxy-drim-7,9(11)-diene 8 and two of 11-bromo-drim-8(9)-en-7-one 10 have been accomplished. For the first time a drimanic compound 12 with an aromatic ring B has been synthesized and the experimental conditions for the selective bromination at C₁₁ and C₁₂ methyl groups of drim-8-en-7-one 2 have been optimized. The synthesized compounds are suitable intermediates for the preparation of natural drimane-type compounds and some of them have shown good antimicrobial and antifungal activities.

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