2-Thioalkyl penems: an efficient synthesis of sulopenem, a (5R, 6S)-6-(1 (R)-hydroxyethyl)-2-[(cis-1-oxo-3-thiolanyl) thio]-2-penem antibacterial
RA Volkmann, PR Kelbaugh, DM Nason…
Index: Volkmann, Robert A.; Kelbaugh, Paul R.; Nason, Deane M.; Jasys, V. John Journal of Organic Chemistry, 1992 , vol. 57, # 16 p. 4352 - 4361
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Citation Number: 56
Abstract
(R)-hydroxyethyl)-2-[(cis-l-oxo-3-thiolanyl) thio]-2-penem-3-carboxylic acids 1 and 2. This synthetic pathway provided in high yield enantiopure thioacetate intermediates 15 and 19. To accommodate the fragile side chain sulfoxide moiety of the targeted@-lactams, standard penem synthetic methodology waa modified to facilitate the conversion of 15 and 19 to 1 and 2. The reactive chloroamtidinone 4b was utilized to generate key azetidinone ...
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