Chemoenzymatic Synthesis of Hygromycin Aminocyclitol Moiety and its C2 Epimer,European Journal of Organic Chemistry

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Chemoenzymatic Synthesis of Hygromycin Aminocyclitol Moiety and its C2 Epimer
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2019-01-02 , DOI: 10.1002/ejoc.201801424
Gonzalo Carrau ₁ , Ana Inés Bellomo ₂ , Leopoldo Suescun ₃ , David Gonzalez ₁

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This article describes the synthesis of hygomycin A aminocyclitol moiety and its C2 epimer from bromobezene by a chemoenzymatic strategy. The sequence involved epoxidation, stereocontrolled oxirane ring opening, dihydroxylation of an electron‐poor olefin, and introduction of a methylenedioxy group. The aminocyclitols were obtained in high chemical and optical purity.