ChemInform Abstract: FUNCTIONALIZATION OF C‐6 OR C‐7 OF PENICILLINS AND CEPHALOSPORINS VIA 1,3‐DIPOLAR INTERMEDIATE

Hirai, Koichi; Iwano, Yuji; Saito, Tatsuhiro; Hiraoka, Tetsuo; Kishida, Yukichi

doi:10.1002/chin.197631342

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2021

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“…A number of different methods to achieve spiro-modification at site a have been reported including: (i) 1,3-dipolar cycloaddition approaches [ 38 , 39 ]; (ii) a phosphane-catalysed [3+2] cycloaddition approach [ 40 ]; and (iii) a rhodium-catalysed cyclopropanation approach [ 19 ]. However, methodologies for spiro-modifications at site b and c are rather limited, and mostly rely on 1,3-dipolar cycloadditon reactions [ 41 ].…”

Section: Introductionmentioning

confidence: 99%

New Methods for the Synthesis of Spirocyclic Cephalosporin Analogues

2021

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Spiro compounds provide attractive targets in drug discovery due to their inherent three-dimensional structures, which enhance protein interactions, aid solubility and facilitate molecular modelling. However, synthetic methodology for the spiro-functionalisation of important classes of penicillin and cephalosporin β-lactam antibiotics is comparatively limited. We report a novel method for the generation of spiro-cephalosporin compounds through a Michael-type addition to the dihydrothiazine ring. Coupling of a range of catechols is achieved under mildly basic conditions (K2CO3, DMF), giving the stereoselective formation of spiro-cephalosporins (d.r. 14:1 to 8:1) in moderate to good yields (28−65%).

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