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  • Title: Synthesis of the C20-C32 tetrahydropyran core of the phorboxazoles and the C22 epimer via a stereodivergent Michael reaction.
    Author: Clarke PA, Ermanis K.
    Journal: Org Lett; 2012 Nov 02; 14(21):5550-3. PubMed ID: 23088315.
    Abstract:
    A stereoselective synthesis of the C20-C32 tetrahydropyran core of the phorboxazoles has been achieved in only seven steps and in a 31% overall yield. The C22 epimer was also synthesized. The key step was a silyl ether deprotection/oxy-Michael cyclization. When this step was conducted under Brønsted acid conditions, the C20-C32 core was formed with the desired 2,6-cis-stereochemistry. However, when the silyl ether deprotection/oxy-Michael cyclization was conducted under fluoride conditions buffered with acetic acid, the C22 epimer of the core was the sole product.
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