Organic Synthesis Question

[KeJoSaBe]

I took organic chemistry about 7 years ago and did fairly well. So, I thought I would be able to help tutor a university student even though I haven't done it since that time; however, we are getting into chemical synthesis and I am starting to realize that there is a lot I don't remember. Can anyone point me in the right direction here? The student has to synthesize the following chemical compound (I have attached the image to this message). We must start with organic reagents no larger than 2 - 3 carbons, or benzene. Any inorganic reagent can be used. Any help is appreciated!

 

 

Thanks

 

[hypervalent_iodine]

You should think about it retrosynthetically. Have a look at the molecule and see if you can think of an obvious disconnection. As a hint: bonds to heteroatoms are a good place to start. It would also help if you could elaborate what level your student is at and what sort of reactions they've been learning about, since there will be ways to synthesise this molecule that they may not have been taught.

[KeJoSaBe]

Hi, thanks so much for this response! It helped to jog my memory a bit.

My student is is taking a 2nd year undergrad class in organic chemistry (2nd of 2 classes). He has gone through the following reactions:
1. substitution of alkyl halides, alcohols etc.
2. Elimination of alkyl halides, alcohols etc.
3. Electrphilic/concerted addition of alkenes and alkynes.
4. Free radicals: substitution and addition
5. Electrophilic aromatic substitution reactions of benzene and its derivatives.

One big question that I have is how to form a 5 membered ring. My initial thought was Diels-Alder but, upon review of my notes I see this forms 6 membered rings. On the other hand, I am going through old notes trying to see if there is a way to convert benzene into a 5 membered ring.

Edited April 11, 2015 by KeJoSaBe

[studiot]

My first question would be are you going to create the cyclic ketone before or after the nitrogen bridge?