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Versuche zur enantiomerenreinen Synthese des Chatancins, 1. Mitt. Synthese von (1R,2S,6S,7R,8S,3′S)-2-(4′-Benzyloxy-3′-methylbutoyl)-7-hydroxy-8-isopropyl-1-methylbicyclo [4.4.0]decan-4-on

Approach to the synthesis of enantiomerically pure chatancin. I. Synthesis of (1R,2S,6S,7R,8S,3′S)-2-(4′-benzyloxy-3′-methylbutoyl)-7-hydroxy-8-isopropyl-1-methylbicyclo [4.4.0]decan-4-on

  • Organische Chemie Und Biochemie
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Summary

Our first target on the way towards the synthesis of enantiomerically pure chatancin is the preparation of the title compound. The cycloadduct of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene and thymoquinone is stereo- and regioselectively reduced to the tricyclic ketoalcohol4, which by nucleophilic cyclisation and reductive removal of the keto group as well as the chlorine atoms yielded a tetracyclic dimethoxyketal. Acidic hydrolysis freed the keto group, which now was treated with a chiral lithium alkyl compound derived from methyl (R)-2-methyl-3-hydroxypropionate in few steps. The resulting stereomeric tertiary alkohols were fragmented and the decalinones thus obtained separated. X-ray analysis permitted the determination of the absolute configuration of these decalinone derivatives.

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Authors and Affiliations

  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien

    W. D. Aichberger, J. Aigner, E. Gössinger & G. Menz

  2. Institut für Physikalische Chemie, Universität Graz, A-8010, Garz

    K. Gruber

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  1. W. D. Aichberger
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  2. J. Aigner
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  3. E. Gössinger
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  4. K. Gruber
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  5. G. Menz
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Aichberger, W.D., Aigner, J., Gössinger, E. et al. Versuche zur enantiomerenreinen Synthese des Chatancins, 1. Mitt. Synthese von (1R,2S,6S,7R,8S,3′S)-2-(4′-Benzyloxy-3′-methylbutoyl)-7-hydroxy-8-isopropyl-1-methylbicyclo [4.4.0]decan-4-on. Monatsh Chem 125, 991–1010 (1994). https://doi.org/10.1007/BF00812715

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  • DOI: https://doi.org/10.1007/BF00812715

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