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  • Title: Thermolysis of isomigrastatin and its congeners via [3,3]-sigmatropic rearrangement: a new route to the synthesis of migrastatin and its analogues.
    Author: Ju J, Lim SK, Jiang H, Seo JW, Her Y, Shen B.
    Journal: Org Lett; 2006 Dec 07; 8(25):5865-8. PubMed ID: 17134292.
    Abstract:
    Thermolysis of isomigrastatin (1) under neat heating conditions afforded migrastatin (1a). The reaction is proposed to proceed via a concerted [3,3]-sigmatropic rearrangement by which ring expansion is achieved regio- and enantiospecifically. The general applicability of this reaction was demonstrated with six additional isomigrastatin congeners (3-8), providing a new route to the synthesis of migrastatin analogues (3a-8a). [reaction: see text]
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