Identifying Nucleophiles Practice Test

Which of the following compounds would be the best nucleophile?

The given molecule is known as voacamine. Multi-cyclic molecules with a high nitrogen content such as this one are known as alkaloids, and tend to be highly toxic. A chemist is attempting to react a sample of voacamine with an electrophilic reagent known as Boc anhydride, which is typically used to "protect" (or react with to chemically mask) nitrogen functionality in order to lessen the toxicity of the molecule. What nucleophilic moiety in voacamine will react first with Boc anhydride?