Sequential acid/base-catalyzed polycyclization of tryptamine derivatives. A rapid access to Büchi's ketone

Nicolas Heureux, Johan Wouters, István E. Markó

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) 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 decribed. 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.

Original languageEnglish
Pages (from-to)5245-5248
Number of pages4
JournalOrganic Letters
Volume7
Issue number23
DOIs
Publication statusPublished - 10 Nov 2005

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