Reserpine core: spot the fabricated intermediate

Single question

Late-stage Pictet-Spengler cyclization closes the indoloquinolizidine C ring of the reserpine core. The reactants and the final product are right. Look at the intermediate after cyclization.

Pictet-Spengler uses indole C2 as the nucleophile

Distinguishing fused vs bridged bicyclic closures

Topology of the indoloquinolizidine framework

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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