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.