Repository logo

Synthetic approach towards cephalezomine A and phomoidride D




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

Journal Title

Journal ISSN

Volume Title


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.


Rights Access


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


Associated Publications