Synthesis of Polycyclic β-Lactams from d-Glucose Derived Chiral Template via Substrate-Controlled Radical Cyclization

Abdul Rakeeb A. S. Deshmukh; Arumugam Jayanthi; Kamanan Thiagarajan; Vedavati G. Puranik; Baburao M. Bhawal

doi:10.1055/s-2004-834890

PAPER

Synthesis of Polycyclic β-Lactams from d-Glucose Derived Chiral Template via Substrate-Controlled Radical Cyclization

Abdul Rakeeb A. S. Deshmukh*^a, Arumugam Jayanthi^a, Kamanan Thiagarajan^a, Vedavati G. Puranik^b, Baburao M. Bhawal^c
^a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
^b Division of Physical Chemistry, National Chemical Laboratory, Pune 411 008, India
^c Emcure Pharmaceuticals Ltd., Emcure House, T-184, M. I. D. C. Bhosari, Pune 411026, India
Fax: +91(20)25893153; Fax: +91(20)25893355; e-Mail: arasd@dalton.ncl.res.in;

Abstract

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Abstract

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.

Key words

azetidin-2-ones - polycyclic β-lactams - radical cyclization - glucose - tributyltin hydride

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