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4 article(s) from Hunter, Luke

Vicinal difluorination as a C=C surrogate: an analog of piperine with enhanced solubility, photostability, and acetylcholinesterase inhibitory activity

Yuvixza Lizarme-Salas,
Alexandra Daryl Ariawan,
Ranjala Ratnayake,
Hendrik Luesch,
Angela Finch and
Luke Hunter

Beilstein J. Org. Chem. 2020, 16, 2663–2670, doi:10.3762/bjoc.16.216

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Figure 1: The natural product piperine (1) is the inspiration for this work; the crystal structure is shown [14]....

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Scheme 1: The attempted synthesis of 6 (a diastereoisomer of 2) via a one-step 1,2-difluorination reaction [24]. ...

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Scheme 2: The attempted synthesis of 2 via a stepwise fluorination approach (ether series). THF = tetrahydrof...

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Scheme 3: Synthesis of compound 2 via a stepwise fluorination approach (ester series). DIC = diisopropylcarbo...

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Figure 2: Conformational analysis of 2 by DFT and NMR. The numbering scheme for NMR spins is given on structu...

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Figure 3: Analog 2 has greater stability to UV light than does piperine (1).

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Figure 4: Biological activity of piperine (1) and derivative 2. (a) Inihbition of AChE by 1 (IC₅₀ >1000 μM) a...

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Published 28 Oct 2020

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Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

Raju Cheerlavancha,
Ahmed Ahmed,
Yun Cheuk Leung,
Aggie Lawer,
Qing-Quan Liu,
Marina Cagnes,
Hee-Chan Jang,
Xiang-Guo Hu and
Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

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Figure 1: Examples of conformationally biased amino acids [1-10]. Compound 6 is a target of this work.

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Scheme 1: The first synthetic approach.

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Scheme 2: The second synthetic approach.

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Scheme 3: The third synthetic approach.

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Scheme 4: The fourth synthetic approach (partially reproduced from ref. [17]).

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Figure 2: Selected J values and the inferred molecular conformations of 6a and 6b.

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Published 01 Nov 2017

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Stereoselectively fluorinated N-heterocycles: a brief survey

Xiang-Guo Hu and
Luke Hunter

Beilstein J. Org. Chem. 2013, 9, 2696–2708, doi:10.3762/bjoc.9.306

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Figure 1: Fluorination alters the reactivity of aziridines.

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Scheme 1: Fluorination makes β-lactam derivatives more reactive towards lipase-catalysed methanolysis.

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Figure 2: The ring pucker in azetidine derivatives can be influenced by a C–F^…N⁺ charge–dipole interaction.

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Figure 3: Fluorination ridifies the pyrrolidine rings of ligand 10, with several consequences for its G-quadr...

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Figure 4: Proline 11 readily undergoes a ring-flip process, but (4R)-fluoroproline 12 is more rigid because o...

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Scheme 2: Hyperconjugation rigidifies the ring pucker of a fluorinated organocatalyst 14, leading to higher e...

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Figure 5: Fluorinated piperidines prefer the axial conformation, due to stabilising C–F^…N⁺ interactions.

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Figure 6: Fluorination can rigidify a substituted azepane, but only if it acts in synergy with the other subs...

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Figure 7: The eight-membered N-heterocycle 24 prefers an axial orientation of the fluorine substituent, givin...

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Figure 8: Some iminosugars are “privileged structures” that serve as valuable drug leads.

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Figure 9: Fluorinated iminosugar analogues 32–34 illuminate the binding interactions of the α-glycosidase inh...

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Figure 10: Fluorinated miglitol analogues, and their inhibitory activity towards yeast α-glycosidase.

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Figure 11: Analogues of isofagomine (31) have different pK_aH values, and therefore exhibit maximal β-glucosida...

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Scheme 3: General strategy for the synthesis of fluorinated N-heterocycles via deoxyfluorination.

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Figure 12: Late stage deoxyfluorination in the synthesis of multifunctional N-heterocycles.

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Scheme 4: During the deoxyfluorination of N-heterocycles, neighbouring group participation can sometimes lead...

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Scheme 5: A building block approach for the synthesis of fluorinated aziridines 2 and 3.

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Scheme 6: Building block approach for the synthesis of a difluorinated analogue of calystegine B (63).

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Scheme 7: Synthesis of fluorinated analogues of brevianamide E (65) and gypsetin (68) via electrophilic fluor...

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Scheme 8: Organocatalysed enantioselective fluorocyclisation.

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Scheme 9: Synthesis of 3-fluoroazetidine 73 via radical fluorination.

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Scheme 10: Synthesis of 3,3-difluoropyrrolidine 78 via a radical cyclisation.

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Scheme 11: Chemoenzymatic synthesis of fluorinated β-lactam 4b.

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Published 29 Nov 2013

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The C–F bond as a conformational tool in organic and biological chemistry

Luke Hunter

Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38

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Figure 1: Conformational effects associated with C–F bonds.

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Figure 2: HIV protease inhibitor Indinavir (17) and fluorinated analogues 18 and 19. In analogue 18 the gauche...

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Figure 3: Cholesteryl ester transfer protein inhibitors 20 and 21. In the fluorinated analogue 21, n_O→σ*_CF hy...

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Figure 4: HIV reverse transcriptase inhibitor 22 and acid-stable fluorinated analogues 23–25. The F–C–C–O gau...

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Figure 5: Dihydroquinidine (26) and fluorinated analogues 27 and 28. Newman projections along the C9–C8 bonds...

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Figure 6: The neurotransmitter GABA (29) and fluorinated analogues (R)-30 and (S)-30. Newman projections of (R...

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Figure 7: The insect pheromone 31 and fluorinated analogues (S)-32 and (R)-32. The proposed bioactive conform...

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Figure 8: Capsaicin (33) and fluorinated analogues (R)-34 and (S)-34.

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Figure 9: Asymmetric epoxidation reaction catalysed by pyrrolidine 35. Inset: the geometry of the activated i...

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Figure 10: The asymmetric transannular aldol reaction catalysed by trans-4-fluoroproline (41), and its applica...

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Figure 11: The asymmetric Stetter reaction catalysed by chiral NHC catalysts 49–52. The ring conformations of ...

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Figure 12: A multi-vicinal fluoroalkane.

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Figure 13: X-ray crystal structures of diastereoisomeric multi-vicinal fluoroalkanes 55 and 56. The different ...

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Figure 14: Examples of fluorinated liquid crystal molecules. Arrows indicate the orientation of the molecular ...

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Figure 15: Di-, tri- and tetra-fluoro liquid crystal molecules 60–62.

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Figure 16: Collagen mimics of general formula (Pro-Yaa-Gly)₁₀ where Yaa is either 4(R)-hydroxyproline (63) or ...

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Figure 17: Enkephalin-related peptide 64 and the fluorinated analogue 65. The electron-withdrawing trifluorome...

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Figure 18: The C–F bond influences the conformation of β-peptides. β-Heptapeptide 66 adopts a helical conforma...

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Figure 19: The conformations of pseudopeptides 69 and 70 are influenced by the α-fluoroamide effect and the fl...

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Published 20 Apr 2010

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