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Dibromomethane as one-carbon source in organic synthesis: total synthesis of (±)- and (−)-methylenolactocin
Authors:Yung-Son Hon  Cheng-Han Hsieh
Institution:a Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi 621, Taiwan, ROC
b Institute of Chemistry, Academia Sinica, Nankang, Taipei 115, Taiwan, ROC
Abstract:A general method was developed to construct monocyclic α-methylene-γ-butyrolactone moiety. The key step is to introduce the α-methylene group by the ozonolysis of mono-substituted alkenes followed by reacting with a preheated mixture of CH2Br2-Et2NH. Application of this key step in the total synthesis of the (±)- and (−)-methylenolactocin was described.
Keywords:Ozonides  α-Methylenation  γ-Butyrolactone  (&minus  )-Methylenolactocin    )-Methylenolactocin
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