Thursday, February 14, 2013

Diels-Alder


Diels-Alder Synthesis of Albicanol

CHE 342
Megan Mier
Compound: Albicanol
     The compound albicanol is formed through a series of synthesis steps including a Diels-Alder reaction. The reaction involves a 1,3 diene and a dienophile alkene. A Diels-Alder reaction forms six membered rings. Three p bonds are broken in a Diels-Alder reaction and two new C-C bonds and one new C=C bond is formed. Diels-Alder reactions are concerted and initiated by heat. In order for the diene to react with the dienophile the diene must be in the s-cis conformation.
     Albicanol is a compound that is used in the production of pharmaceutical antifungal creams. The compound is synthesized from liverworts and mulluscs.3 The synthesis of albicanol yields an racemic mixture of enantioselective products.
IUPAC Name: [(1S,4aS,8aS)-5,5,8a-Trimethyl-2-methylenedecahydro-1-naphthalenyl]methanol.1
Chemical Formula: C15H26O
Structure: ACD/ChemSketch
 
 
 
 
 
 
 
 
 
 
Reaction Scheme: 
Diels-Alder Reactants-          
 
Image: ACD ChemSketch
 


 
 
 
 
 
 
 
References:
1ChemSpider. CSID:149808, http://www.chemspider.com/Chemical-Structure.149808.html (accessed 14:19, Feb 13, 2013)
 
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1 comment:

  1. I like Diels Alder reaction but I don't know why I have always been unable to cope up with it. I was never able to remember it completely. Anyway thanks for sharing.

    -Tatvachintan

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