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  • Title: Synthesis of stereoisomers of Artemisia and Chrysanthemum bis(acetylenic) enol ether spiroacetals.
    Author: Wu B, Feast GC, Thompson AL, Robertson J.
    Journal: J Org Chem; 2012 Dec 07; 77(23):10623-30. PubMed ID: 23113738.
    Abstract:
    An 11-step synthesis is described of two diastereomeric candidates for a bis(acetylenic) enol ether spiroacetal isolated from Chrysanthemum boreale. Key steps in the synthetic route include spiroacetal lactone alkylidenation and subseqent modified Cadiot-Chodkiewicz cross-coupling to install the bis(acetylenic) enol ether functionality. From NMR comparisons, neither of the candidates, whose structures were confirmed by single-crystal X-ray diffraction, correspond to the natural product, and a proposal for the correct structure is put forward.
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