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  • Title: A direct route to fluostatin C by a fascinating Diels-Alder reaction.
    Author: Yu M, Danishefsky SJ.
    Journal: J Am Chem Soc; 2008 Mar 05; 130(9):2783-5. PubMed ID: 18254631.
    Abstract:
    The Diels-Alder reactions between vinylindenes (5 or 6) as the dienes with quinoneketals (7 or 8) or with methacrolein as the dienophiles were investigated. The remarkable regioselectivities of these Diels-Alder adducts suggested that the regiopreferences of these dienes and dienophiles in these cases are not a fixed property of each component of the cycloaddition but are mutually contigent. This paper shows how the Diels-Alder reaction between 6 and 8 was applied to the inaugural total syntheses of fluostatin C and E.
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