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 retrieved from : http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000700005&lng=en&nrm=iso&tlng=en
References:
1ChemSpider. CSID:149808,
http://www.chemspider.com/Chemical-Structure.149808.html (accessed 14:19, Feb
13, 2013)
2Rahman, Atta. Studies in Natural Products Chemistry:
Bioactive Natural Products. Retrieved February 13, 2013 from http://books.google.com/books?id=VJH0qqj5bhQC&pg=PA408&lpg=PA408&dq=what+is+the+compound+albicanol+used+for&source=bl&ots=_QWEGuy0y3&sig=optKVyqqjnOxAqp62sHOmb4bmO8&hl=en&sa=X&ei=Tl4cUYuFIue32wWOlIH4Dw&ved=0CG0Q6AEwBw#v=onepage&q=what%20is%20the%20compound%20albicanol%20used%20for&f=false
Blog URL:
