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- Title
Synthesis of the Pentacyclic Framework of the Alkaloid Tronocarpine.
- Authors
Torres‐Ochoa, Rubén O.; Reyes‐Gutiérrez, Paul E.; Martínez, Roberto
- Abstract
A short and efficient synthesis of the pentacyclic core of the indole alkaloid tronocarpine is described. The synthetic pathway involves several easily accomplished steps, including a radical oxidative aromatic substitution reaction on the N- tert-butoxycarbonyl-protected tryptamine and a xanthate, a 1,4-1,2-nucleophilic addition between a 2,3-disubstituted indole and an α,β-unsaturated aldehyde, and a Ti-mediated Dieckmann condensation. This report represents a significant advance in the quest for the first total synthesis of tronocarpine.
- Subjects
INDOLE alkaloid synthesis; CHEMICAL reactions; TRYPTAMINE; ALDEHYDE derivatives; ORGANIC synthesis research
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 1, p48
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301388