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2010-07-12

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Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/164357

A general methodology for the enantioselective synthesis of 1-substituted tetrahydroisoquinoline alkaloids

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https://doi.org/10.1002/ejoc.201000473

Abstract

Starting from tricyclic lactam 2 , which is easily accessible by cyclocondensation of δ‐oxoester 1 with (R )‐phenylglycinol, a three‐step synthetic route to enantiopure 1‐substituted tetrahydroisoquinolines, including 1‐alkyl‐, 1‐aryl‐, and 1‐benzyltetrahydroisoquinoline alkaloids, as well as the tricyclic alkaloid (-)‐crispine A, has been developed. The key step is a stereoselective α‐amidoalkylation reaction using the appropriate Grignard reagent.

Subject

Alcaloides, Lactames, Síntesi asimètrica

Subject (English)

Alkaloids, Lactams, Asymmetric synthesis

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

Citation

AMAT TUSÓN, Mercedes, et al. A general methodology for the enantioselective synthesis of 1-substituted tetrahydroisoquinoline alkaloids. European Journal of Organic Chemistry. 2010. Vol. 2010, num. 21, pags. 4017-4026. ISSN 1434-193X. [consulted: 6 of June of 2026]. Available at: https://hdl.handle.net/2445/164357

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