842172-43-4Relevant articles and documents
Synthesis of polycyclic β-lactams from D-glucose derived chiral template via substrate-controlled radical cyclization
Deshmukh, Abdul Rakeeb A. S.,Jayanthi, Arumugam,Thiagarajan, Kamanan,Puranik, Vedavati G.,Bhawal, Baburao M.
, p. 2965 - 2974 (2004)
A highly stereoselective and substrate-controlled synthesis of polycyclic β-lactams from D-glucose derived chiral template via intramolecular radical cyclization is described. The cyclization is highly substrate dependant, proceeding via 6-exo and 7-endo heptenyl type radical cyclization with the radical acceptor allyl group at N-1 and the radical progenitor on a sugar moiety, anchored to the β-lactam ring at C-4. The mode of radical cyclization in N-propargyl substrates is highly stereospecific and controlled by the stereochemistry of the β-lactam ring.