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

Abstract

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.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]

GRAPHICAL ABSTRACT

Keywords:

• Bromination
• drim-7,9(11)-diene
• drim-8-en-7-one
• electrooxidation
• photooxygenation
• synthesis

ACKNOWLEDGMENTS

The support from Project No. 264115 (STREAM) in the frame of EU founded FP7-REGPOT-2010-1 and European Regional Development Fund, Sectoral Operational Program “Increase of Economic Competitiveness,” Priority Axis 2 (SOP IEC-A2-O2.1.2-2009-2, ID 570, COD SMIS-CSNR: 12473, Contract 129/2010-POLISILMET) are acknowledged by the authors from the “Petru Poni” Institute. One of the authors (C.E.) thanks the National Project for Young Scientists from Republic of Moldova, No. 12.819.08.05F, “New Synthetic Pathways towards the Polyfunctional Terpenic Compounds with Potential Biological Activity,” 2012–2013.