Cortisone CD-ring: spot the regiochemistry flaw

Single question

Robinson annulation onto the angular-methyl cyclopentanone to build the steroid C ring. Reagents, conditions, and reaction class are right. Check which carbon of the cyclopentanone forms the new C-C bond.

Regiochemistry of Robinson annulation Michael addition

Why the kinetic enolate is alpha to the carbonyl, not gamma

Steroid ring-fusion stereochemistry

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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