In hope of a less inflammatory year that mends the divide within communities across the globe we turn to the synthesis of a compound W that has a similar structure to the promising new anti-inflammatory drug Licofelone that possesses the following structure :
We start our synthesis using the methyl ester of proline . It undergoes the following set of reactions, a key step involves a Huisgen cycloaddition
We now define certain variables (all numbers are positive) :
What is the value of ?
Hint :
Compound C has no amide group
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We start our deductions from the methyl ester of proline whose structure is as follows :
The formation of A is a simple acetylation reaction, by observing that A has a formula C 8 H 1 3 O 3 N , one can deduce that the reaction conditions favour a selective removal of the methyl group to generate a carboxylic acid B .
The next set of deductions start from compound D whose formula is known, the reaction conditions that lead to the formation of D favour a Huisgen cycloaddition (The alkyne and expulsion of C O 2 give this away), hence we find the formula of compound C to be C 7 H 9 O 2 N . This tells us that the transformation of compound B to C is a simple dehydration reaction that should result in a ketene . However, the hint provided tells us that no amide group is present in C implying that the ketene reacts to form a mesoionic bicyclic compound.
With most of the compound present, deducing the structure of W is a simple task. Knowing that W has a similar backbone as Licofelone , the large boron rings must be replaced with phenyl rings.
From the illustrations,
The answer is 2016 + 1 = 2 0 1 7
Inspirations :
Professor D.M. Volochnyuk's problem in the 4 9 t h IMO.