Synthesis of the oxygenated pactamycin core.
[structure: see text]. Pactamycin, one of the most complex and densely functionalized aminocyclitol antibiotics known, presents synthetic challenges that include reactivity and sterics, relative and absolute stereochemistry, and functional group compatibility and protection. An approach is reported that features four different types of (cyclopentane) face selective functionalization reactions and results in a polyfunctionalized and appropriately protected intermediate that incorporates all the core carbons and the oxygenated functionality of the target.
Knapp
Spencer
S
Department of Chemistry & Chemical Biology, Rutgers The State University of New Jersey, Piscataway, NJ 08854, USA. spencer.knapp@rutgers.edu
Yu
Younong
Y
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry*; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D010142:Pactamycin / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D003517:Cyclopentanes; C007201:cyclopentanone; D010142:Pactamycin; D010100:Oxygen