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2012-06-17

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/164274

Sequential ring-closing metathesis-vinyl halide Heck cyclization reactions: access to the tetracyclic ring system of ervitsine

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Abstract

A chemoselective indole-templated ring-closing metathesis is used to assemble the cyclohepta[b]indole substructure of the indole alkaloid ervitsine. A subsequent intramolecular Heck coupling of the resulting alkene functionality with an amino-tethered vinyl halide accomplishes the closure of the unique 2- azabicyclo[4.3.1]decane framework of the alkaloid with concomitant incorporation of the exocyclic Eethylidene substituent.

Subject

Metàtesi (Química), Reaccions químiques, Productes naturals, Síntesi orgànica, Alcaloides

Subject (English)

Metathesis (Chemistry), Chemical reactions, Natural products, Organic synthesis, Alkaloids

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Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

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BENNASAR FÈLIX, M. Lluïsa, et al. Sequential ring-closing metathesis-vinyl halide Heck cyclization reactions: access to the tetracyclic ring system of ervitsine. Tetrahedron. 2012. Vol. 68, num. 24, pags. 4641-4648. ISSN 0040-4020. [consulted: 7 of June of 2026]. Available at: https://hdl.handle.net/2445/164274

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