Synthesis and resolution of albicanic acid. Simple access to optically active drimane sesquiterpenes
- 1 January 1987
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 987-992
- https://doi.org/10.1039/p19870000987
Abstract
The synthesis of albicanic acid (±)-(2) and the resolution to its enantiomers (+)-(2) and (–)-(2) are described. Determination of their optical purity was by 1H n.m.r. spectroscopy of the corresponding methyl esters (+)-(1) and (–)-(1) with Eu(dcm)3. The absolute configuration of the acids (+)-(2) and (–)-(2) has been determined by transformation to their alcohols (–)-(5) and (+)-(5) and interrelation with the natural albicanol. An efficient formal total synthesis of both enantiomeric forms of three drimanic sesquiterpenes, drimenin (7), isodrimenin (8), and drim-7-ene-11,12-diol (9), presenting special synthetic interest, is reported, starting from the corresponding enantiomers of albicanic acid (2).This publication has 7 references indexed in Scilit:
- Syntheses of the insect antifeedant (.+-.)-cinnamodial and the drimane sesquiterpenoids (.+-.)-isodrimenin and (.+-.)-fragrolideThe Journal of Organic Chemistry, 1985
- Improved total synthesis of (±)-drimeninJournal of the Chemical Society, Perkin Transactions 1, 1985
- Sesquiterpenoid constituents of eight porostome nudibranchsThe Journal of Organic Chemistry, 1983
- The Diels–Alder route to drimane related sesquiterpenes; synthesis of cinnamolide, polygodial, isodrimeninol, drimenin and warburganalJournal of the Chemical Society, Perkin Transactions 1, 1983
- A new, efficient synthesis of (+)-isodrimeninJournal of the Chemical Society, Perkin Transactions 1, 1982
- Catalytic asymmetric induction in oxidation reactions. Synthesis of optically active epoxynaphthoquinonesThe Journal of Organic Chemistry, 1980
- Potent army worm antifeedants from the east African Warburgia plantsJournal of the Chemical Society, Chemical Communications, 1976