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Organic Letter (Feng, Y.; Pattarawarapan, M.; Wang, Z.; Burgess, K. “Solid-Phase SN2 Macrocyclization Reactions To Form ß-Turn Mimics” Org. Lett. 1999, 1, 121-124.)

 

Questions:
1. Where is the primary author of the paper from? (Name of University or company)

2. What is a ß-Turn Mimic? Why are they important?

 

 

 
3. What is solid-phase synthesis?

 

 

4. What is a macrocycle?
5. Referencing Scheme 1, please draw the mechanism for the conversion of molecule 5to molecule 1. Step (ii) removes the resin (grey ball), so don’t worry about that.

 

 

 

 

6. Why doesn’t an E2 reaction occur from instead?

 

 

 
7. Pick two more terms out of the paper that you do not know, look them up, and explain them.

 

 

 

 

 
8. Pick a reference that the author(s) cited that you think is especially important and write it below. Why do you think it is important? Obtain a copy of this reference and attach it to this assignment. Make sure you choose a reference you can get online or at the library. DO NOT PAY FOR THIS!!!

 

 

 

 
9. Refer to the supporting information for this paper (online). For the procedure of compound 1a, scroll down to the part that starts with, “The macrocyclization step was carried out by…”

a. What base was used for this reaction?

b. How many molar equivalents of base was used?
c. What is the physical appearance of the final product (eg. Yellow liquid, purple solid, green gas, etc.)?

 
d. The purity was determined by HPLC. What is HPLC? Explain how this works.
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