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

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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.

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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: 29 of June of 2026]. Available at: https://hdl.handle.net/2445/164357

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