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Full-Text Articles in Chemistry
Unleashing A “True” Pser-Mimic In The Cell, Kaushik Panigrahi, David L. Nelson, David B. Berkowitz
Unleashing A “True” Pser-Mimic In The Cell, Kaushik Panigrahi, David L. Nelson, David B. Berkowitz
David Berkowitz Publications
In this issue of Chemistry & Biology, Arrendale and coworkers demonstrate a new prodrug strategy for intracellular delivery of an α, α-(difluoromethylene)phosphonate phosphoserine mimic. The deprotected pseudo-phosphopeptide releases the pro-apoptotic FOXO3a-transcription factor from its 14-3-3-adaptor protein complex, resulting in leukemic cell death.
Halocarbocyclization Entry Into The Oxabicyclo[4.3.1]Decyl Exomethylene-Δ-Lactone Cores Of Linearifolin And Zaluzanin A - Exploiting Combinatorial Catalysis, Sandeep K. Ginotra, Jacob A. Friest, David B. Berkowitz
Halocarbocyclization Entry Into The Oxabicyclo[4.3.1]Decyl Exomethylene-Δ-Lactone Cores Of Linearifolin And Zaluzanin A - Exploiting Combinatorial Catalysis, Sandeep K. Ginotra, Jacob A. Friest, David B. Berkowitz
David Berkowitz Publications
A streamlined entry into the sesquiterpene lactones (SQL) cores of linearifolin and zaluzanin A is described. Stereochemistry is controlled through transformations uncovered by ISES (In-Situ- Enzymatic-Screening). Absolute stereochemistry derives from kinetic resolution of 5- benzyloxypentene-1,2-oxide, utilizing a β-pinene-derived-Co(III)-salen. Relative stereochemistry (1,3-cis-fusion)is set via formal halometalation/carbocyclization, mediated by [Rh(O2CC3F7)2]2/ LiBr. Subsequent ring-closing metathesis (RCM-Grubbs II) yields the title exomethylene-δ- lactone SQL-cores. In complementary fashion, RCM with Grubbs-I catalyst provides the oxabicyclo[3.3.1]nonyl-core of xerophilusin R and zinagrandinolide.