Fitxers

659133.pdf (474.84 KB)

Tipus de document

Article

Versió

Versió acceptada

Data de publicació

2016-02-12

Tots els drets reservats

Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/127732

Exploration of Ring‐Closing Enyne Metathesis for the Synthesis of Azonino[5,4‐b]indoles

Títol de la revista

Autors

Director/Tutor

ISSN de la revista

Títol del volum

Recurs relacionat

https://doi.org/10.1002/ejoc.201501517

Resum

The use of the ring‐closing enyne metathesis (RCEYM) as a methodology for the synthesis of the azonino[5,4‐b]indole system, featuring the tricyclic substructure of the alkaloids cleavamine and quebrachamine, has been explored. Three series of enyne substrates were studied for their compatibility with the RCEYM reaction. In addition to the usual substrates bearing either a terminal or an internal alkyne, for the first time enynes with an alkynyl halide moiety were also considered. Although the metathesis cyclization allowed for assembly of the azoninoindole nucleus in all three series, an effective catalytic cycle was only noted for internal alkyne substrates. On the basis of the experimental results, the "yne‐then‐ene" pathway seems to be the mechanism at play in these reactions.

Matèries

Metàtesi (Química), Síntesi orgànica, Alcaloides, Ciclització (Química), Compostos cíclics

Matèries (anglès)

Metathesis (Chemistry), Organic synthesis, Alkaloids, Ring formation (Chemistry), Cyclic compounds

Citació

Col·leccions

Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)

Citació

SOLÉ ARJÓ, Daniel, et al. Exploration of Ring‐Closing Enyne Metathesis for the Synthesis of Azonino[5,4‐b]indoles. European Journal of Organic Chemistry. 2016. Vol. 2016, num. 7, pags. 1355-1366. ISSN 1434-193X. [consulted: 9 of September of 2026]. Available at: https://hdl.handle.net/2445/127732

Exportar metadades

JSON - METS

Compartir registre