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Solution-Phase and Solid-Phase Syntheses of Enzyme Inhibitor RK-682 and Antibiotic Agglomerins

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journal contribution
posted on 22.07.2005, 00:00 by Rainer Schobert, Carsten Jagusch
The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition−Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph3PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation−elimination sequence led to antibiotic agglomerins A−C 2 featuring 3-acyl-5-methylidenetetronic acid structures.