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Synthesis 1994; 1994(11): 1185-1194
DOI: 10.1055/s-1994-25669
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Inter- and Intramolecular Hetero-Diels-Alder Reactions; Part 50: Domino Reactions in Organic Chemistry: The Knoevenagel-hetero-Diels-Alder-Hydrogenation Sequence for the Biomimetic Synthesis of Indole Alkaloids via Strictosidine Analogues

Lutz F. Tietze* , Jürgen Bachmann, Jürgen Wichmann, Olaf Burkhardt
  • *Institut für Organische Chemie der Georg-August Universität, Tammannstraße 2, D-37077 Göttingen, Germany
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Publication Date:
25 April 2002 (online)

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A new biomimetic access to indole alkaloid derivatives via strictosidine analogues is described using a highly efficient and selective domino reaction consisting of a tandem Knoevenagel-hetero-Diels-Alder-hydrogenation sequence. In a three component reaction of the aldehyde 27f, the 1,3-dicarbonyl compound 28 and the enol ether 30a a 1 : 1-mixture of 31c and 31d is obtained in 91% yield which after hydrogenation gives the indole alkaloid derivative 35a belonging to the pseudo series as a single compound. Similarly, reaction of 27f, 28 and 30b also affords 35a after hydrogenation as the only compound. In the domino reaction of 27e, 28 and 30a the indole alkaloid derivative 36b of the normal type is formed in 46% yield.

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