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. 2008;47(9):1736-40.
doi: 10.1002/anie.200705421.

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

Aaron C Smith  1 , Robert M Williams
Affiliations

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

Aaron C Smith et al. Angew Chem Int Ed Engl. 2008.

Abstract

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 re-affirm the formal total synthesis of quinine reported by Woodward and Doering in 1944.

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Figures

Figure 1
Figure 1
Crystals of quinine tartrate obtained directly from quinotoxine according to the Rabe-Kindler protocol[2] without the use of any modern isolation, chromatographic or analytical techniques.
Scheme 1
Scheme 1
Conversion of d-quinotoxine to quinine. a) NaOBr, NaOH, HCl (aq), Et2O, 55% crude; b) NaOEt, EtOH, 88% crude; c) Aluminum powder, NaOEt, EtOH, 5% (as the tartrate salt).
Scheme 2
Scheme 2
Preparation of d-quinotoxine from natural quinine.[11]
See this image and copyright information in PMC

References

    1. Woodward RB, Doering WE. J. Am. Chem. Soc. 1944;66:849.
    2. Woodward RB, Doering WE. J. Am. Chem. Soc. 1945;67:860–874.
    1. Rabe P, Kindler K. Ber. Dtsch. Chem. Ges. 1918;51:466–467.
    1. Rabe P. Ber. Dtsch. Chem. Ges. 1911;44:2088–2091.
    1. Rabe P. Justus Liebigs Ann. Chem. 1932;492:242–266.
    1. Turner RB, Woodward RB. The Chemistry of the Cinchona Alkaloids. In: Manske RHF, editor. The Alkaloids. Vol. 3. New York: Academic Press; 1953. Chap. 16.
    2. Uskokovic´ MR, Grethe G. The Cinchona Alkaloids. In: Manske RHF, editor. The Alkaloids. Vol. 14. New York: Academic Press; 1973. p. 181.
    3. Kaufman TS, Rfflveda EA. Angew. Chem. Int. Ed. 2005;44:854–885. - PubMed

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