Honors Capstone Project
Date of Submission
John D. Chisholm
Arts and Science
Capstone Prize Winner
Won Capstone Funding
Sciences and Engineering
Biochemistry | Biochemistry, Biophysics, and Structural Biology
Pumiliotoxin 341 A differs from all other pumiliotoxins in that its alkylidene side chain has been cyclized to form a pyranose ring, providing another quaternary center in its indolizidine ring. Although the gross structure of this natural product has been determined, the absolute and relative stereochemistry of the tertiary alcohol on C14 is still unknown. As a result, we want to synthesize this alkaloid to prove its stereochemistry and to prepare material for further biological analysis. A rhodium-catalyzed alkyne addition reaction currently being developed in our group is employed as the key reaction in our synthesis of the indolizidine core. For this reaction, we envisioned a protected aminoalkyne being used as a nucleophile with a dicarbonyl acceptor. Several different aminoalkynes were prepared and used to test this approach.
Choi, Lydia, "Total Synthesis of Pumiliotoxin 341A" (2006). Syracuse University Honors Program Capstone Projects. 626.
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