A General Methodology for the Enantioselective Synthesis of 1-Substituted Tetrahydroisoquinoline Alkaloids

作者:Amat Mercedes*; Elias Viviane; Llor Nuria; Subrizi Fabiana; Molins Elies; Bosch Joan
来源:European Journal of Organic Chemistry, 2010, (21): 4017-4026.
DOI:10.1002/ejoc.201000473

摘要

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

  • 出版日期2010-7