143159-86-8Relevant academic research and scientific papers
A Novel Approach to Cephalosporins From Allenylazetidinones: A New Cyclization Strategy via Tandem Cuprate Addition-Sulfenylation
Kant, Joydeep,Roth, Jeanine A.,Fuller, Carl E.,Walker, Donald G.,Benigni, Daniel A.,Farina, Vittorio
, p. 4956 - 4966 (2007/10/02)
An efficient approach to the synthesis of 3-substituted cephems bearing carbon-based substituents of choice at the C(3) position from inexpensive penicillins is described.The strategy involves the synthesis of an allenylazetidinone from penicillin sulfoxide followed by the addition of an organocuprate at low temperature.Organocuprates undergo 1,4-conjugate addition at the central allenic carbon of the allenylazetidinone to form a carbon-carbon bond which is followed by ring closure via an intramolecular sulfenylation reaction.The chemistry has been applied to the synthesis of a variety of 3-substituted cephems bearing substituents such as alkyl, cycloalkyl, aryl, alkenyl, and allyl.Precursors to the synthesis of important antibiotics, i.e.Cefadroxil, Cefixime, and Cefzil, are also available from this novel approach.The methodology is not limited to carbon-based 3-substituted cephems, but provides access to some 3-norcephalosporins as well.
Processes for making cephems from allenylazetidinone derivatives
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, (2008/06/13)
This invention relates to a novel process for making a cephem of formula II from a 2-(3-amino-2-oxo-azetidin-1-yl)-2,3-butadienoate intermediate of formula I using an organo-copper reagent. In another aspect, this invention is concerned with said intermed
Processes for making cephems from allenylazetidinone derivatives
-
, (2008/06/13)
This invention relates to a novel process for making a cephem of formula II from 2-(3-amino-2-oxo-azetidin-1-yl)-2,3-butadienoate of formula I. In another aspect, this invention is concerned with a process of further converting a compound of formula II in
A new strategy for the conversion of penams into cephems via allene chemistry
Farina, Vittorio,Kant, Joydeep
, p. 3559 - 3562 (2007/10/02)
We describe an extension of the Morin rearrangement in which 3-norcephalosporins bearing sulfur substituents at C(3) are obtained directly from an allenic intermediate, which is efficiently prepared from penicillin V sulfoxide.
