We are grateful to the National Institutes of Health for financial support (GM068011). Mass spectra were obtained on instruments supported by the NIH Shared Instrument Grant GM49631. We are particularly grateful to Prof. William von Eggers Doering of Harvard University for insightful and provocative discussions. We are indebted to Dr. Jeffrey I. Seeman for many thoughtful discussions and encouragement. We thank our co-workers, Dr. Thomas J. Greshock and Brandon English, for independently checking and repeating our best determined experimental conditions using the Rabe–Kindler conversion of d-quinotoxine into quinine procedure.
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Communication
Rabe Rest in Peace: Confirmation of the Rabe–Kindler Conversion of d-Quinotoxine Into Quinine: Experimental Affirmation of the Woodward–Doering Formal Total Synthesis of Quinine†
Article first published online: 31 JAN 2008
DOI: 10.1002/anie.200705421
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Smith, A. and Williams, R. (2008), Rabe Rest in Peace: Confirmation of the Rabe–Kindler Conversion of d-Quinotoxine Into Quinine: Experimental Affirmation of the Woodward–Doering Formal Total Synthesis of Quinine. Angewandte Chemie International Edition, 47: 1736–1740. doi: 10.1002/anie.200705421
- †
Publication History
- Issue published online: 11 FEB 2008
- Article first published online: 31 JAN 2008
- Manuscript Received: 26 NOV 2007
Funded by
- National Institutes of Health. Grant Number: GM068011
Keywords:
- aluminum;
- natural products;
- quinine;
- reduction
Graphical Abstract
Put to rest: The three-step conversion of d-quinotoxine into quinine, as originally reported by Rabe and Kindler in 1918, has been experimentally verified. This conversion serves to reaffirm the formal total synthesis of quinine reported by Woodward and Doering in 1944.