This work explores a de novo asymmetric synthesis of several analogues of the biologically active carbohydrate natural product phomopsolide E. The proposed synthetic route improves upon routes previously developed by the O’Doherty Group for the 7-oxo and 7-aza analogues of phomopsolide E. The new route ascertains the stereocontrol by incorporating a second reagent-controlled Noyori reduction for the flexible introduction of the C-9 alcohol. Once complete the synthesis will allow for the efficient stereoselective synthesis of all eight possible stereoisomers of phomopsolide E analogue for a stereochemical structure activity relationship (S-SAR) of this anticancer natural product analogue.

De novo synthesis of phomopsolide E analogues

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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