Organic Chemistry - Camphor Synthesis

AI Thread Summary
The discussion focuses on the biosynthesis of camphor from acetyl-CoA and acetic acid, emphasizing a biological approach. The process involves the phosphorylation of Co-A by ATP, creating a leaving group that facilitates the formation of a bicyclic structure. Carbon-13 labeled acetic acid was used in experiments with the plant Cinnamomum camphora to isolate camphor, raising questions about the incorporation of the labeled carbon in the final product. Participants are seeking clarification on the steps involved in this biosynthetic pathway and whether the bicyclic bridge contains the C-13 enriched carbon. The conversation highlights the complexity of synthesizing camphor biologically compared to simpler methods using isoprenes.
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Hello guys and girls. I am writing to you all today in hopes that someone out there will be able to help me with my problem. I am asked to synthesize the molecule camphor starting merely from acetly-CoA and Acetic Acid. This must be done in a biological manner. Ie. The Co-A group will be phosporylated by two moles of ATP giving you a fanastic leaving group (OPP) which then can leave the join the linear molecule into its bicylco podcut.

Here is the question in full.

Outline all of the steps involved in the biosynthesis of the monterpene camphor from acetyl-CoA. Carbon 13 labeled acetic acid was prepared from Carbob 13 enriched CO2 and normal CH3MgBr. This acetic acid was then fed to the plant Cinnamomum camphora and camphor was isolated a few days later. Outline the biosynthesis and state wheter or not the bicylcobridge in camphor contains the C13 enriched Carbon or not.

Now for what i know; i know you can synthesize cmaphor easily from only two molecules of Isoprenes. However, in this scenario since it is asking for a biological perspective i am not sure if the body is capable of riping of an acidic hydrogen like LDA would and then forming a B-keto acid with the attached Co-A portion.

Any help would be extremely helpfull.
 
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Try out this link

http://www.iisc.ernet.in/academy/resonance/Oct1996/pdf/Oct1996p37-43.pdf
 
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