Synthesis of Bis(indole) Alkaloids from Arundo donax: The Ynindole Diels–Alder Reaction,Conformational Chirality,and Absolute Stereochemistry |
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| Authors: | Dr. Jingjin Chen Andrew J. Ferreira Prof. Dr. Christopher M. Beaudry |
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| Affiliation: | Department of Chemistry, Oregon State University, Corvallis, OR 97331 (USA) |
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| Abstract: | Bis(indole) alkaloids from Arundo donax were synthesized using the first ynindole Diels–Alder reaction. The alkaloids are chiral, having stable enantiomeric conformations with half‐lives of racemization of t1/2=4150–25100 seconds at room temperature. Their absolute stereochemistry was determined using the exciton chirality method. |
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| Keywords: | alkynes chirality cycloaddition natural products total synthesis |
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