[loves2Spl00ge]

I'm stuck on how this mechanism should start. My gut is saying the primary amine attacks either the aldehyde carbonyls or the CH2 pi orbitals. Any suggestions?

[critzz]

Start out on the condensation of the primary amine and the shorter one of the two aldehydes. From there on you could try and figure out the mechanism, using arrow-pushing of electrons.

Have you learned about the Pictet-Spengler and Sakurai reactions yet?

[loves2Spl00ge]

We didn't go over those two reactions, but I did google them, and it made things much clearer. Will the step after the pictet-spengler reaction be an intramolecular sakurai?

[critzz]

Yes, could you draw the mechanism you got right now?

[phth]

Step 1) list the possibilities by making an educated guess what plausible mechanisms are.
Step 2)
Step 3) choose the one that leads to the product.

[critzz]

Step 4) profit