Formation of stereochemically defined exocyclic double bonds, present in a number of natural products, can possess a considerable synthetic challenge.Herein we disclose an efficient, stereoselective synthesis of intermediate amino acid 2  via the Ireland-Claisen rearrangement of a boron enolate derived from 8-membered lactone 1 , and the further elaboration of this building block into 8-Deoxypumiliotoxin 193H. The synthesis of 8-membered lactone 1  from L-valine and L-homoproline, the optimization studies of the key transformation � the Ireland-Claisen rearrangement and the completion of total synthesis will be presented.

Application of Ireland-Claisen rearrangement in the total synthesis of 8-Deoxypumiliotoxin 193H

248th National Meeting (2014)

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