Kyle Rugg

Abstract

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

Publication Date

2013

Document Type

Thesis

Student Type

Graduate

Degree Name

Chemistry (MS)

Department, Program, or Center

School of Chemistry and Materials Science (COS)

Advisor

Dr. Jeremy A. Cody

Comments

Note: imported from RIT’s Digital Media Library running on DSpace to RIT Scholar Works in July 2014. Physical copy available from RIT's Wallace Library at QD262 .R84 2013

Campus

RIT – Main Campus

Plan Codes

CHEM-MS

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