Skip to main content

The University Project - 30 Day Blogging Challenge (Day 4)

This post is different because I wont be discussing someone else's research, I am discussing my own research. My final year project at university. 

What was my project about?

The Synthesis of a derivative of Montiporyne E. The aim of the project was to find a simple, fast and effective method of reactions to produce a derivative of Montiporyne E potential anti-cancer drug.

Cancer is caused when cells replicate abnormally and rapidly to form tumours. This is because the cell does not undergo apoptosis (the normal programmed cell death) and therefore these affected cells continue to multiply uncontrollably. 

Montiporyne E is derived from a hard coral, named Montipora SpHard corals have been found to produce cytotoxic, acetylenic compounds. It is used in the treatments of solid tumour cells. The extraction from hard coral is expensive, laborious and also hard coral is on the verge of extinction, therefore a more effective method of production was required.
Montiporyne E
The reaction scheme for the production of the derivative of Montiporyne E

My Step-By-Step Method:

Step 1 :

  1. • 3-ethoxy-2 cylohexone was dissolved in THF and Grignard reagent was added dropwise, in a nitrogen atmosphere and continuous stirring for 30 minutes.

Step 2 - The Oxime Reaction:

  1. •3-methyl- 2 cyclohexenone (product from step 1), hydroxylamine hydrochloride and sodium hydroxide were added in a round bottomed flask and stirred for 1 and a half to 2 hours.
  2. • The product was then extracted using diethyl ether and then neutralised with Glacial acetic acid
  3. • This was then dried with Magnesium sulphate and further dried on a rotary evaporator.

    Step 3 - The Beckmann rearrangement - Ring expansion (from a 6 -7 membered ring)

  1.       The oxime (from step 2), was added to toluene in a two necked Round Bottomed Flask with a magnetic stirrer and attached to condenser and heated to 90°C.
  2.       Chlorosulfonic acid was added dropwise to the mixture.
  3.       The reaction was left stirring for half an hour then cooled to room temperature. 
  4.       After the mixture cooled, Sodium hydroxide (—NaOH) was added to the mixture, dropwise to neutralise the product. 

Step 1: Production of 3-methyl-2-cyclohexanone

Step 2: Oxime reaction
Step 3: Beckmann Rearrangement 

What would I have done differently ?

In the beginning of my project I found out that if I was successful in finishing the project on time, I could have an opportunity to test my final product on cells (in the biology labs) to test my product for its cytotoxicity. So my goal for the whole year was based around making the final product.  Unfortunately I couldn't test it in the biology labs because there was an earlier deadline for application.

It would have been better if I had more time dedicated to the project so I could have focused on each of the separate reactions to find one that gave the best yield and better method of purification.