Eletefine is a natural product of the stephaoxocane family of alkaloids. It possesses an isoquinoline moiety functionalized with three methoxy groups forming an electron rich aromatic system. Eletefine also possesses a ten-membered ring with a novel bridged vinyl ether functionality, and a remote chiral alcohol, making it a conspicuous and desirable target for the synthetic organic chemist. The plant from which eletefine was first isolated (Cissampelos glaberrima) has been used in traditional medicine for the relief of symptoms from urinary tract infections and asthma. The proposed synthesis of eletefine is a convergent route which features a Sonogashira coupling and a novel alkyne hydration. Herein, methods towards the synthesis of the model system des-hydroxyeletefine are described, in particular attempts towards formation of the AB ring system of des-hydroxyeletefine, as well as C8-C9 bond formation methodology via acylation and Sonogashira coupling.
Library of Congress Subject Headings
Organic compounds--Synthesis; Alkaloids--Synthesis; Isoquinoline
Department, Program, or Center
School of Chemistry and Materials Science (COS)
Dr. Jeremy A. Cody
Rugg, Kyle, "Studies Toward the Total Synthesis of Eletefine" (2013). Thesis. Rochester Institute of Technology. Accessed from
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