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Total synthesis and determination of the absolute configuration of (+)-neoisoprelaurefucin
Authors:Hyunjoo LeeHyoungsu Kim  Seungyoup BaekSanghee Kim  Deukjoon Kim
Institution:a Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, San 56-1, Shillim-Dong, Kwanak-Gu, Seoul 151-742, Republic of Korea
b Natural Products Research Institute, College of Pharmacy, Seoul National University, 28 Yungun, Jongro-Ku, Seoul 110-460, Republic of Korea
Abstract:The first total synthesis of the seven-membered ring ether marine natural product (+)-neoisoprelaurefucin (1) has been achieved employing a regioselective internal alkylation of amide 3, a novel sequence for removal of the triethylsilyl group from the resulting triethylsilyloxepene 2, and a bromoetherification of alcohol 16 as key steps. In addition, the absolute stereochemistry of the natural product was assigned.
Keywords:internal alkylation  total synthesis  marine natural product  seven-membered ether ring
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