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  • Title: Stereoselective synthesis of the octahydronaphthalene unit of integramycin via an intramolecular Diels-Alder reaction.
    Author: Dineen TA, Roush WR.
    Journal: Org Lett; 2005 Mar 31; 7(7):1355-8. PubMed ID: 15787505.
    Abstract:
    [reaction: see text] The racemic cis-decalin core fragment 30 of integramycin was synthesized by a sequence involving a highly diastereoselective intramolecular Diels-Alder reaction of triene 24. A remarkable switch in stereoselectivity occurred upon changing the dienophile unit of 24 from (Z)- to (E)-geometry.
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