[Organic Chemistry II] Looking for some feedback on an extra credit synthesis project.

[ik314]

I have to synthesize a made-up molecule from a simple starting compound (preferably 3 carbons or less).  My professor will know if I copy-paste a synthesis from online, so that definitely wouldn't fly.  In order for me to get the maximum number of points, the synthesis must meet the following criteria:

1) There must be 4-8 steps (protonations and deprotonations not counting)

2) I must use reagents that we learned in both Organic 1 and 2.  We can’t use anything we haven’t learned yet.  NO DIELS-ALDER ALLOWED FOR CYCLIZATION, THE ONLY WAY WE HAVE LEARNED IS INTRAMOLECULAR SN2.) 
Here’s everything I have learned so far this semester:                         

3) chemoselectivity 

4) regioselectivity

5) a cyclization (ring formation)

6) stereoselectivity

7) annotations explaining why a certain intermediate/product was formed (wherever relevant)


The project is due tomorrow at 5pm (Eastern time).

Here is an example (https://i.imgur.com/CdS6BCW.jpg) of a synthesis that would get the max # of points. And here is mine (https://i.imgur.com/DOch3eT.png) so far.

What I need help with is making sure my synthesis contains the aforementioned 7 things, and that every step is accurate. The help would be much appreciated. 

Edited April 9, 2018 by ik314
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