[This corrects the article DOI: 10.1039/D2RA05224E.].
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Correction: Glycal mediated synthesis of piperidine alkaloids: fagomine, 4--fagomine, 2-deoxynojirimycin, and an advanced intermediate, iminoglycal.
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[This corrects the article DOI: 10.1039/D2RA05224E.].
View Article and Find Full Text PDFSynthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-D-pyrrolosamine Glycal of Lomaiviticin A & B via Epimerization of L-Threonine.
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Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street Cambridge, MA 02138.
An efficient synthesis of the N-(tert-butyloxycarbonyl)-O-triisopropylsilyl-D-pyrrolosamine glycal of lomaiviticin A (1) and lomaiviticin B (2) is described. The synthesis is highlighted by the epimerization of the L-threonine-derived oxazolidine 10 to oxazolidine 11. This key epimerization reaction, which serves to establish the correct relative configuration of the carbohydrate unit, was made possible only after conformational analysis indicated that substituted oxazolidines may adopt conformations that preclude enolization.
View Article and Find Full Text PDFDynamics of alkene radical cation/phosphate anion pair formation from nucleotide C4' radicals. The DNA/RNA paradox revisited.
J Am Chem Soc
September 2001
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
The fragmentation of nucleotide C4' radicals generated by thiyl radical addition to C4'C5' exocyclic glycals has been re-examined and found to be a function of the thiol and, probably, the initiating system employed. It has been demonstrated that C4' radicals of DNA and RNA models fragment even in the very nonpolar benzene solution if the correct (aliphatic) thiol is employed. (17)O-Labeling experiments are used to demonstrate that the fragmentation of nucleotide C4' radicals (2-deoxyribo- and ribo-) to contact ion pairs is either irreversible or so rapidly reversible as to preclude prior reorganization of the contact ion pair.
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