- Unexpected Retroaldol-Aldol Reaction during O-Alkylation of Hydroxylated Vince Lactam Derivatives
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The unexpected retroaldol-aldol reaction during O-alkylation of a β-hydroxy lactam was found to be highly dependent on the temperature and shows a remarkable solvent effect. In DMF, O-alkylation is faster than retroaldol-aldol rearrangement giving exclusively products with retention of configuration. In THF, O-alkylation is slower than rearrangement, giving selectively products with inversion of stereochemistry. In DMSO, a retroaldol reaction followed by fast intramolecular proton transfer occurs to give the ring-opened aldehyde.
- Bengtsson, Christoffer,Wetzel, Alexander,Bergman, Joakim,Br?nalt, Jonas
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- HORMONE RECEPTOR MODULATORS FOR TREATING METABOLIC MUTAGENIC AND FIBROTIC CONDITIONS AND DISORDERS
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The invention relates to activators of FXR useful in the treatment of autoimmune disorders, liver disease, intestinal disease, kidney disease, cancer, and other diseases in which FXR plays a role, having the Formula (I): wherein L1, A, X1
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Page/Page column 102
(2019/04/11)
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- Fluorinated conformationally restricted γ-aminobutyric acid aminotransferase inhibitors
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On the basis of the structures of several potent inhibitor molecules for γ-aminobutryric acid aminotransferase (GABA-AT) that were previously reported, six modified fluorine-containing conformationally restricted analogues were designed, synthesized, and tested as GABA-AT inhibitors. The syntheses of all six molecules followed from a readily synthesized ketone intermediate. Three of the molecules were found to be irreversible inhibitors of GABA-AT with comparable or larger kinact/K1 values than that of vigabatrin, a clinically used antiepilepsy drug, and the other three were reversible inhibitors. A possible mechanism for inactivation by one of the inactivators is proposed.
- Lu, Hejun,Silverman, Richard B.
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p. 7404 - 7412
(2008/02/01)
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- Conversion of one enantiomer of the carbocyclic nucleoside synthon 2-azabicyclohept-5-en-3-one into the other
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The lactam synthon 2-azabicyclohept-5-en-3-one was converted into its enantiomer by a 5-step sequence incorporating a skeletal rearrangement mediated by anchimeric assistance of the nitrogen atom; the route proceeded via a tosylate intermediate prone to racemization.
- Palmer, Christopher F.,McCague, Raymond
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p. 1201 - 1204
(2007/10/02)
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