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Model Studies Towards the Total Synthesis of Lyconadin A via An Acyl Radical Cascade Reaction Model Studies Towards the Total Synthesis of Lyconadin A via An Acyl Radical Cascade Reaction

by Zhu, Koudi 1977-

Abstract (Summary)
Lyconadin A is an alkaloid possessing a unique structure and antitumor activity. The total synthesis of Lyconadin A was proposed via an acyl radical cascade reaction. To investigate the possibility and stereoselectivity of the cascade cyclization, phenyl selenoester 16 was chosen as a model substrate to study the 7-exo-5-exo radical cyclization. A synthetic route to phenyl selenoester 16 was developed. The 7-exo-5-exo radical cyclization was found to occur with a high yield and excellent stereoselectivty. Attempts were also tried to synthesize another radical precursor 14 albeit with less success. A synthetic pathway to the synthesis of 14 as well as its potential use in the context of the synthesis of Lyconadin A was proposed.
Bibliographical Information:

Advisor:

School:Brigham Young University

School Location:USA - Utah

Source Type:Master's Thesis

Keywords:lyconadin a total synthesis 7 exo 5 radical cascade cyclization

ISBN:

Date of Publication:04/03/2006

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