SYNTHESIS OF ANATOXIN-A

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The major long-term objective of this project is the synthesis of anatoxin-a using chemistry which will allow large quantities to be prepared as well as numerous analogs. Initially, the carbocyclic analog will be prepared starting with the Diels-Alder adduct of cyclopentadiene and maleic anhydride. Reaction with dimethylcuprate, a Hunsdiecker reaction and loss of hydrogen bromide gives acetylnorbornene. Cycloaddition with acetylene or 1,2-dichloroethylene should give a bicyclo(4.2.1)dienone which can be reduced to the desired analog of anatoxin-a. The alkaloid itself will be prepared using similar chemistry starting from pyrrole.