Synthesis of the Pentacyclic Framework of the Alkaloid Tronocarpine

0427580 - ÚOCHB 2015 RIV DE eng J - Článek v odborném periodiku
Torres-Ochoa, R. O. - Reyes Gutierrez, Paul Eduardo - Martínez, R.
Synthesis of the Pentacyclic Framework of the Alkaloid Tronocarpine.
European Journal of Organic Chemistry. Roč. 2014, č. 1 (2014), s. 48-52. ISSN 1434-193X. E-ISSN 1099-0690
Institucionální podpora: RVO:61388963
Klíčová slova: natural products * alkaloids * radicals * nucleophilic addition * cyclization
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 3.065, rok: 2014

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 ,-unsaturated aldehyde, and a Ti-mediated Dieckmann condensation. This report represents a significant advance in the quest for the first total synthesis of tronocarpine.
Trvalý link: http://hdl.handle.net/11104/0233147