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  • Title: Concise approach to the carbocyclic core of the naturally occurring sphingomyelinase inhibitor scyphostatin.
    Author: Mehta G, Modugu NR.
    Journal: J Org Chem; 2013 Apr 05; 78(7):3367-73. PubMed ID: 23442124.
    Abstract:
    A flexible strategy toward the carbocyclic core of the naturally occurring sphingomyelinase inhibitor scyphostatin, from the readily available Diels-Alder adducts of cyclopentadiene and 2-allyl-p-benzoquinone, has been devised. This approach leverages the stereochemical predisposition of the norbornyl-fused scaffolds to generate the desired stereochemical pattern and leads to a concise synthesis of the epoxycyclohexenoid core of scyphostatin with a manipulable allyl side arm.
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