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  • Title: Enantioselective total synthesis of atpenin A5.
    Author: Ohtawa M, Ogihara S, Sugiyama K, Shiomi K, Harigaya Y, Nagamitsu T, Omura S.
    Journal: J Antibiot (Tokyo); 2009 Jun; 62(6):289-94. PubMed ID: 19373276.
    Abstract:
    Enantioselective total synthesis of atpenin A5, a potent mitochondrial complex II (succinate-ubiquinone oxidoreductase) inhibitor, has been achieved by a convergent approach through a coupling reaction between 5-iodo-2,3,4,6-tetraalkoxypyridine and a side-chain aldehyde. The two key segments were synthesized through ortho-metalation/boronation with (MeO)3B/oxidation with mCPBA, ortho-iodination, halogen dance reaction, Sharpless epoxidation and regioselective epoxide-opening reaction. This synthetic study resulted in the revision of the earlier reported 1H-NMR data of the natural atpenin A5 and the confirmation of the stereochemical assignment.
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