Abstract

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 proline-catalyzed asymmetric α-hydrazination reaction as the key step. The highly enantioselective introduction of an amino group is exploited to synthesize (−)-calycotomine, (−)-salsolidine, (−)-carnegine, (+)-homolaudanosine, (+)-homoprotoberberine and (+)-crispine A.

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