Synthesis of 4-Benzloxyindole by Condensation with Dimethylformamide Dimethyl Acetal Followed by Reduction and Optimization of a Novel Indole Synthesis with a Model System
Loading...
Authors
Thomas, John E.
Issue Date
2002
Type
Thesis
Language
en_US
Keywords
Alternative Title
Abstract
Diazonamide A is a marine natural product that exhibits cytotoxic activity and possesses an unprecedented macrocyclic structure. Recently the Vedej s group has made advances in assembling the macrocyclic core. A key intermediate ofthis synthesis is an oxazolyl indole, the synthesis ofwhich relies on 4-benzyloxyindole. In this project 4benzyloxyindole
was synthesized by literature methods. The overall yield for this 4-step synthesis was 75.4 %, all the procedures were scaleable (>50g scale) and the product was isolated in very pure form. Prior Vedejs group work suggested that a route with fewer steps may be available to synthesize the oxazolyl indole intermediate. This novel method was used to explore a shorter path to a model system for the oxazole indole, and the optimization ofthis reaction was undertaken varying several parameters.
Description
Citation
Publisher
License
U.S. copyright laws protect this material. Commercial use or distribution of this material is not permitted without prior written permission of the copyright holder.