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α-N-phthalimido-oxy isobutyrate-mediated deoxygenative arylation: total synthesis of alanenses A and B
Young Eum Hyun1, Jeonguk Kweon2,1, Thi Hieu Linh Phan1
1Department of Chemistry, Korea Advanced Institute of Science and Technology (KAIST) Daejeon 34141 Republic of Korea sunkyu.han@kaist.ac.kr.
Abstract:
Inspired by a biosynthetic hypothesis of alanense A, we developed two distinct methods for the deoxygenative arylation of α-N-phthalimido-oxy isobutyrate (NPIB), derived from hydroxyl groups adjacent to or conjugated with a carbonyl moiety. One approach utilizes photoredox catalysis to achieve a radical-mediated arylation reaction. The other approach involves an acid-mediated arylation method that proceeds through a cationic intermediate. The acid-mediated approach was successfully applied to the total syntheses of alanenses A, B, and O7'-methyllacinilene E.
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