Synthesis of R-(−)-Imperanene from the Natural Lignan Hydroxymatairesinol
- 11 September 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (21) , 7544-7546
- https://doi.org/10.1021/jo025985c
Abstract
A convenient and high yielding method for the synthesis of R-(−)-imperanene, starting from the readily available natural lignan hydroxymatairesinol from Norway spruce, was developed. Hydroxymatairesinol was degraded in strongly basic aqueous conditions to (E)-4-(4-hydroxy-3-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenylmethyl)but-3-enoic acid, which was esterified and then reduced by LiAlH4 to afford R-(−)-imperanene. The configuration at the crucial stereocenter was preserved in the synthesis, and the obtained product was identified by optical rotation measurements and chiral HPLC analyses as the R-(−)-enantiomer (ee 86−92%).Keywords
This publication has 6 references indexed in Scilit:
- Total Synthesis of (S)-(+)-Imperanene. Effective Use of Regio- and Enantioselective Intramolecular Carbon−Hydrogen Insertion Reactions Catalyzed by Chiral Dirhodium(II) CarboxamidatesThe Journal of Organic Chemistry, 2002
- Enantioselective Synthesis of Imperanene, a Platelet Aggregation InhibitorOrganic Letters, 2001
- Nomenclature of Lignans and Neolignans (IUPAC Recommendations 2000)Pure and Applied Chemistry, 2000
- Aplysillin A, a Thrombin Receptor Antagonist from the Marine Sponge Aplysina fistularis fulvaJournal of Natural Products, 1995
- Imperanene, a Novel Phenolic Compound with Platelet Aggregation Inhibitory Activity from Imperata cylindricaJournal of Natural Products, 1995
- Colpol, a New Cytotoxic C6-C4-C6 Metabolite from the Alga Colpomenia sinuosaJournal of Natural Products, 1993