90628-99-2Relevant academic research and scientific papers
A Novel Ring-Closure Strategy for the Carbapenems: The Total Synthesis of (+)-Thienamycin
Hanessian, Stephen,Desilets, Denis,Bennani, Youssef L.
, p. 3098 - 3103 (2007/10/02)
Intramolecular Michael cyclization of an N--4-(3-nitro-2-propenyl)-3-oxoazetidin-2-one available in optically pure form leads to the corresponding carbapenam skeleton.Further elaboration via oxidative cleavage of an exocyclic nitromethylene group gives an advanced intermediate, which was transformed into (+)-thienamycin.The stereochemistry of the Michael cyclization and the pitfalls of protective group chemistry are discussed.
AN EFFICIENT CARBAPENEM SYNTHESIS VIA AN INTRAMOLECULAR WITTIG REACTION OF NEW TRIALKOXYPHOSPHORANE-THIOLESTERS
Yoshida, Akira,Tajima, Yawara,Takeda, Noriko,Oida, Sadao
, p. 2793 - 2796 (2007/10/02)
New trialkoxyphosphorane-thiolesters 10, obtained by reaction of oxalimides 9 with trialkyl phosphite, were efficiently cyclized by an intramolecular Wittig reaction to give carbapenems 11.
