Asymmetric synthesis of six tetrahydroisoquinoline natural products through α-amination of an aldehyde

An enantioselective route towards the synthesis of C-1 substituted tetrahydroisoquinoline natural products is reported. Six different natural products are synthesized from a single aldehyde using prolinecatalyzed asymmetric alpha-hydrazination reaction as the key step. The highly enantioselective introduction of an amino group is exploited to synthesize (-)-calycotomine, (-)-salsolidine, (-)-carnegine, (+)-homolaudanosine, (+)-homoprotoberberine and (thorn)-crispine A. (C) 2021 Elsevier Ltd. All rights reserved.

Automated summary

An enantioselective route has been developed for the synthesis of C-1 substituted tetrahydroisoquinoline natural products. Six different natural products were successfully synthesized from a single aldehyde using proline-catalyzed asymmetric alpha-hydrazination reaction. The highly enantioselective introduction of an amino group allowed for the synthesis of (-)-calycotomine, (-)-salsolidine, (-)-carnegine, (+)-homolaudanosine, (+)-homoprotoberberine and (thorn)-crispine A.