The structure of laricinolic acid and its biomimetic transformation into officinalic acid
Bernhard ErbLaboratorium für Organische Chemie, ETH Zürich, Universitätstrasse 16, Zürich, SwitzerlandHans‐Jürg BorschbergLaboratorium für Organische Chemie, ETH Zürich, Universitätstrasse 16, Zürich, SwitzerlandD. ArigoniLaboratorium für Organische Chemie, ETH Zürich, Universitätstrasse 16, Zürich, Switzerland
2000en
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Abstract
Laricinolic acid (8), a new sesquiterpene of the drimane type, has been isolated from the wood-rotting fungus Laricifomes officinalis. Its structure was elucidated by spectroscopic means and confirmed via a correlation with the known drimenine derivative 13. Oxidation of 8 to 1, followed by a mild thermal treatment, furnished (−)-officinalic acid (4) in 65% yield. This transformation establishes the hitherto unknown absolute configuration of the latter. An independent correlation was achieved by pyrolysis of 4 which furnished (−)-dihydrooxoisodrimenine (14) of known absolute configuration.
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