Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins.
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 Ph(3)PCCO 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.
Schobert
Rainer
R
Organisch-Chemisches Laboratorium, Universität Bayreuth, 95440 Bayreuth, Germany. rainer.schobert@uni-bayreuth.de
Jagusch
Carsten
C
D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000215:Acylation; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D005663:Furans / Q000737:chemistry; D005988:Glyceric Acids / Q000737:chemistry; D015394:Molecular Structure; D019308:Palmitic Acid / Q000737:chemistry; D010749:Phosphoprotein Phosphatases / Q000037:antagonists & inhibitors* / Q000138:chemical synthesis
D000900:Anti-Bacterial Agents; D004791:Enzyme Inhibitors; D005663:Furans; D005988:Glyceric Acids; C094097:RK 682; C063061:agglomerin A; C063062:agglomerin B; C063063:agglomerin C; D019308:Palmitic Acid; C042971:glyceric acid; D010749:Phosphoprotein Phosphatases; C003422:tetronic acid; D015107:4-Butyrolactone