- Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams
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Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C?H and N?H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chemical complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work we report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.
- Wagener, Tobias,Lückemeier, Lukas,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 6425 - 6429
(2021/02/22)
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- (R)-α-aminoadipic acid: An interesting chiral pool building block
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(R)-α-Aminoadipic acid is available on a large scale by enzymatic cleavage from cephalosporin C (CephC) in the production of 7- aminocephalosporanic acid (7-ACA). It can be converted into other interesting enantiomerically pure compounds, e.g. derivatives of (R)-pipecolic acid (Rpiperidine 2-carboxylic acid), (R)-6-oxopiperidine-2-carboxylic acid, (R)-1,2,3,4-tetrahydropyridine 2(2H)-carboxylates, and other compounds obtained by further conversions of these products. ARKAT-USA, Inc.
- Sadiq, Amina,Sewald, Norbert
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scheme or table
p. 28 - 36
(2012/03/08)
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- Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists
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2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the 1-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be ≥95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K i 5-130 nM) at EP4 and subtype selectivity.
- Elworthy, Todd R.,Brill, Emma R.,Caires, Christopher C.,Kim, Woongki,Lach, Leang K.,Tracy, Jahari Laurant,Chiou, San-San
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p. 2523 - 2526
(2007/10/03)
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- EP4 receptor agonist, compositions and methods thereof
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This invention relates to potent selective agonists of the EP4 subtype of prostaglandin E2 receptors, their use or a formulation thereof in the treatment of glaucoma and other conditions, which are related to elevated intraocular pressure in the eye of a patient. This invention further relates to the use of the compounds of this invention for mediating the bone modeling and remodeling processes of the osteoblasts and osteoclasts.
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Page/Page column 11
(2010/02/14)
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- 2-Piperidone derivatives as prostaglandin agonists
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The invention provides compounds of the Formula: wherein m, n, A, X, Y, Z, R1, R2, R4, R6, R7, R8, R9 and R10 are as defined herein, and pharmaceutically acceptable sa
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- EP4 receptor agonist, compositions and methods thereof
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This invention relates to potent selective agonists of the EP4 subtype of prostaglandin E2 receptors, their use or a formulation thereof in the treatment of glaucoma and other conditions, which are related to elevated intraocular pressure in the eye of a patient. This invention further relates to the use of the compounds of this invention for mediating the bone modeling and remodeling processes of the osteoblasts and osteoclasts.
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Page/Page column 11
(2010/02/08)
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- A total synthesis of nannochelin A. A short route to optically active Nω-hydroxy-α-amino acid derivatives
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The total synthesis of nannochelin A, a lysine-basd cinnamoyl hydroxamate produced by Nannocystis exedens, is described. The key transformation involves construction of the Nε-cinnamoyl-Nε-hydroxy-L-lysine methyl ester fragment by partial reduction of the lactam carbonyl of 6 derived from L-lysine, oximation of this aldehyde equivalent compound 8 with O-[2-(trimethylsilyl)ethyl]hydroxylamine, and reduction of the oxime 10, followed by N-acylation prior to coupling with the external carbonyls of citric acid. This methodology will be applicable to synthesis of other hydroxamate-containing siderophores bearing hydrogenolyzable groups in the molecule.
- Sakamoto, Takeshi,Li, Hao,Kikugawa, Yasuo
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p. 8496 - 8499
(2007/10/03)
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