β-Lactams from Carbohydrates

Abstract

Since more then thirty years carbohydrates have gained much attention as chiral starting materials in stereocontrolled target oriented synthesis. Among variety of applications, synthesis of β-lactam antibiotics from carbohydrate precursors played a special role owing to the importance of these class of compounds in modern chemotherapy. In 1994 we published a review article on the synthesis of β-lactams from carbohydrate precursors. The present survey reports literature published after that date. The streaking feature of the syntheses performed during the last decade is domination of the highly stereoselective direct formation of a four-membered β-lactam ring via [2 + 2]cycloaddition of ketenes to imines and of chlorosulfonyl isocyanate to olefins. Particularly attractive substrates are: in former method, imines derived from glyceraldehyde and in latter one, vinyl ethers of acetal protected sugars.