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Updated: Aug 15, 2026

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
Sequential acid/base-catalyzed polycyclization of tryptamine derivatives. A rapid access to Büchi's ketone
Nicolas Heureux1, Johan Wouters, István E Markó
1Department of Chemistry, Université Catholique de Louvain, Louvain-la-Neuve, Belgium.
Abstract:
[reaction: see text] The development of an efficient and diastereoselective methodology that allows the rapid construction of the tetracyclic core of the Aspidosperma and Strychnos alkaloid families is described. Our approach relies upon two key steps: a sequential silica gel/potassium tert-butoxide polycyclization of a tryptamine precursor and a tandem oxidative decarboxylation/ring-closing reaction. The assembly of Büchi's ketone, a key intermediate in the synthesis of vindorosine, has been accomplished using this approach.
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