This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and BASF AG. Special thanks are due to Dipl.-Chem. J. Kammerer for help with the enzymatic work, and to Prof. Dr. H. Fritz and Dr. D. Hunkler and Dr. J. Wörth for the NMR and MS analyses, respectively.
Article first published online: 30 DEC 2003
Copyright © 1989 by VCH Verlagsgesellschaft mbH, Germany
Angewandte Chemie International Edition in English
Volume 28, Issue 9, pages 1253–1255, September 1989
How to Cite
Falk-Heppner, M., Keller, M. and Prinzbach, H. (1989), Unsaturated 1,4-cis and 1,4-trans-Diaminotetradeoxycycloheptites—Enantiomerically Pure, Polyfunctionalized Tropa Derivatives by Enzymatic Hydrolysis. Angew. Chem. Int. Ed. Engl., 28: 1253–1255. doi: 10.1002/anie.198912531
Dedicated to Professor Christoph Rüchardt on the occasion of his 60th birthday
- Issue published online: 30 DEC 2003
- Article first published online: 30 DEC 2003
- Manuscript Received: 28 APR 1989
The compound anti-cis-diepoxycycloheptene alcohol 1 (R H), prepared from tropilidene (tropone), is the starting material for an efficient synthesis of a variety of protected, enantiomerically pure 1, 4-diaminotetradeoxycycloheptites appropriate for glycosidation reactions. Enzymatic hydrolysis of the tropa-analogous meso-diacetate intermediates leads in 86–100% yield to monoacetates with ee values above 99%.