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Synthetic approach towards cephalezomine A and phomoidride D

Date

2011

Authors

Dong, Ping, author
Wood, John Louis, advisor
Williams, Robert M., committee member
Rovis, Tomislav, committee member
Bernstein, Elliot R., committee member
Partin, Kathryn M., committee member

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Abstract

Two synthetic approaches towards cephalezomine A and phomoidride D are described separately. The first approach towards cephalezomine A invented a new method for the synthesis of 3-butoxy-1-chlorobutenone and successful constructed α-O and ß' -N disubstituted dienone for a designed key intermediate of cascade cyclization by Eschenmoser coupling of thiolactam and 3-butoxy-1-chlorobutenone. The second approach towards phomoidride D systematically studied the electronic effects of different ester substituents for the phenolic oxidation and inverse electron demand Diels-Alder reaction, which resulted in the synthesis of functionalized bicyclic [2.2.1] intermediate. Base on this, a new route for the synthesis of precursor of Grob fragmentation has been established towards the total synthesis of phomoidride D by samarium diiodide mediated radical cascade cyclization.

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Subject

Eschenmoser coupling
synthetic approach
samarium diiodide mediated radical cascade cyclization
phenolic oxidation and Diels-Alder reaction
phomoidride D
cephalezomine A

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