The structure of laricinolic acid and its biomimetic transformation into officinalic acid

Citation
B. Erb et al., The structure of laricinolic acid and its biomimetic transformation into officinalic acid, J CHEM S P1, (15), 2000, pp. 2307-2309
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
15
Year of publication
2000
Pages
2307 - 2309
Database
ISI
SICI code
1470-4358(2000):15<2307:TSOLAA>2.0.ZU;2-R
Abstract
Laricinolic acid (8), a new sesquiterpene of the drimane type, has been iso lated from the wood-rotting fungus Laricifomes officinalis. Its structure w as elucidated by spectroscopic means and confirmed via a correlation with t he known drimenine derivative 13. Oxidation of 8 to 1, followed by a mild t hermal treatment, furnished (-)-officinalic acid (4) in 65% yield. This tra nsformation establishes the hitherto unknown absolute configuration of the latter. An independent correlation was achieved by pyrolysis of 4 which fur nished (-)-dihydrooxoisodrimenine (14) of known absolute configuration.