Enantioselective formal synthesis of ent-rhynchophylline and ent-isorhynchophylline

Starting from (S)-tryptophanol, a formal synthesis of ent-rhyncho-phylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.

Bibliographic Details
Authors: Amat Tusón, Mercedes, Ramos, Carlos, Pérez Bosch, Maria, Molins i Grau, Elies, Florindo, Pedro, Santos, Maria M. M., Bosch Cartes, Joan
Format: article
Status:Versión aceptada para publicación
Publication Date:2013
Country:España
Institution:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repository:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2445/36425
Online Access:https://hdl.handle.net/2445/36425
Access Level:Open access
Keyword:Alcaloides
Síntesi asimètrica
Estereoquímica
Alkaloids
Asymmetric synthesis
Stereochemistry
Description
Summary:Starting from (S)-tryptophanol, a formal synthesis of ent-rhyncho-phylline and ent-isorhynchophylline, involving stereoselective cyclocondensation, spirocyclization, and alkylation reactions, and the final adjustment of the oxidation level at the oxindole and piperidine moieties, is reported.