25997-37-9Relevant academic research and scientific papers
Axinellamines as broad-spectrum antibacterial agents: Scalable synthesis and biology
Rodriguez, Rodrigo A.,Barrios Steed, Danielle,Kawamata, Yu,Su, Shun,Smith, Peter A.,Steed, Tyler C.,Romesberg, Floyd E.,Baran, Phil S.
, p. 15403 - 15413 (2014)
Antibiotic-resistant bacteria present an ongoing challenge to both chemists and biologists as they seek novel compounds and modes of action to out-maneuver continually evolving resistance pathways, especially against Gram-negative strains. The dimeric pyrrole-imidazole alkaloids represent a unique marine natural product class with diverse primary biological activity and chemical architecture. This full account traces the strategy used to develop a second-generation route to key spirocycle 9, culminating in a practical synthesis of the axinellamines and enabling their discovery as broad-spectrum antibacterial agents, with promising activity against both Gram-positive and Gram-negative bacteria. While their detailed mode of antibacterial action remains unclear, the axinellamines appear to cause secondary membrane destabilization and impart an aberrant cellular morphology consistent with the inhibition of normal septum formation. This study serves as a rare example of a natural product initially reported to be devoid of biological activity surfacing as an active antibacterial agent with an intriguing mode of action.
Palauchlor: A practical and reactive chlorinating reagent
Rodriguez, Rodrigo A.,Pan, Chung-Mao,Yabe, Yuki,Kawamata, Yu,Eastgate, Martin D.,Baran, Phil S.
supporting information, p. 6908 - 6911 (2014/06/09)
Unlike its other halogen atom siblings, the utility of chlorinated arenes and (hetero)arenes are twofold: they are useful in tuning electronic structure as well as acting as points for diversification via cross-coupling. Herein we report the invention of a new guanidine-based chlorinating reagent, CBMG or "Palauchlor", inspired by a key chlorospirocyclization en route to pyrrole imidazole alkaloids. This direct, mild, operationally simple, and safe chlorinating method is compatible with a range of nitrogen-containing heterocycles as well as select classes of arenes, conjugated π-systems, sulfonamides, and silyl enol ethers. Comparisons with other known chlorinating reagents revealed CBMG to be the premier reagent.
