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Author Kathlyn A Parker

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Importance of a 4-Alkyl Substituent for Activity in the Englerin Series.

Daniel C Elliott, John A Beutler, Kathlyn A Parker,

The ring closing metathesis/transannular etherification approach to the englerin nucleus was adapted to provide two key intermediates for analogue synthesis: the 4-desmethyl Δ5,6 tricycle and the 4-oxo Δ5,6 tricycle. The former was elaborated to 4-desmethyl englerin A and the latter served as a common precursor for englerin A, 4-ethyl englerin ... Read more >>

ACS Med Chem Lett (ACS medicinal chemistry letters)
[2017, 8(7):746-750]

Cited: 0 times

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Precision Synthesis of Alternating Copolymers via Ring-Opening Polymerization of 1-Substituted Cyclobutenes.

Kathlyn A Parker, Nicole S Sampson,

Investigation of complex molecular systems depends on our ability to correlate physical measurements with molecular structure. Interpretation of studies that rely on synthetic polymers is generally limited by their heterogeneity; i.e., there is variation in the number and arrangement of the monomeric building blocks that have been incorporated. Superior physics ... Read more >>

Acc. Chem. Res. (Accounts of chemical research)
[2016, 49(3):408-417]

Cited: 12 times

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Five Easy Pieces. The Total Synthesis of Phosphoiodyn A (and Placotylene A).

David J Galler, Kathlyn A Parker,

The convergent total synthesis of the marine natural product phosphoiodyn A, a nanomolar agonist of human peroxisome proliferator-activated receptor delta (hPPARδ), was achieved in five steps total from commercially available and inexpensive starting materials. The synthesis relies on the unprecedented regioselective hydrozirconation of a terminal acetylene in the presence of ... Read more >>

Org. Lett. (Organic letters)
[2015, 17(22):5544-5546]

Cited: 3 times

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Ru-Catalyzed Isomerization Provides Access to Alternating Copolymers via Ring-Opening Metathesis Polymerization.

Li Tan, Guofang Li, Kathlyn A Parker, Nicole S Sampson,

We describe an isomerization-alternating ROMP protocol that gives linear copolymers with rigorous sequence alternation. Bicyclo[4.2.0]oct-7-ene-7-carboxamides of primary amines are isomerized in the presence of (3-BrPyr)2Cl2(H2IMes)Ru=CHPh to the corresponding bicyclo[4.2.0]oct-1(8)-ene-8-carboxamides in which the olefinic bond is tetrasubstituted. The isomerized amides undergo alternating ring-opening metathesis polymerization with cyclohexene to provide soluble and ... Read more >>

Macromolecules (Macromolecules)
[2015, 48(14):4793-4800]

Cited: 7 times

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A Bicyclo[4.2.0]octene-Derived Monomer Provides Completely Linear Alternating Copolymers via Alternating Ring-Opening Metathesis Polymerization (AROMP).

Li Tan, Kathlyn A Parker, Nicole S Sampson,

Strained bicyclic carbomethoxy olefins were utilized as substrates in alternating ring-opening metathesis polymerization and found to provide low-dispersity polymers with novel backbones. The polymerization of methyl bicyclo[4.2.0]oct-7-ene-7-carboxylate with cyclohexene in the presence of the fast-initiating Grubbs catalyst (H2IMes)(3-Br-Pyr)2Cl2Ru=CHPh leads to a completely linear as well as alternating copolymer, as demonstrated ... Read more >>

Macromolecules (Macromolecules)
[2014, 47(19):6572-6579]

Cited: 7 times

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Intermolecular radical cation Diels-Alder (RCDA) reaction of bicyclooctadienes: biomimetic formal total synthesis of kingianin A and total syntheses of kingianins D, F, H, and J.

Hee Nam Lim, Kathlyn A Parker,

Three endo bicyclooctadienol dimers corresponding to kingianins A and H, D, and F and J were obtained by the intermolecular radical cation Diels-Alder (RCDA) reaction. Each isomer was cleanly isolated without the aid of preparative HPLC. Kingianins D, F, H, and J were prepared by way of these intermediates from ... Read more >>

J. Org. Chem. (The Journal of organic chemistry)
[2014, 79(3):919-926]

Cited: 2 times

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Total synthesis of kingianin A.

Hee Nam Lim, Kathlyn A Parker,

A 12-step synthesis of kingianin A, an inhibitor of the antiapoptotic protein Bcl-xL, is based on a radical cation Diels-Alder reaction (RCDA). This approach is thought to be biomimetic. The use of a tether in the key RCDA step controls the regiochemistry of the cycloaddition, leading to the desired core ... Read more >>

Org. Lett. (Organic letters)
[2013, 15(2):398-401]

Cited: 9 times

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Bifunctional inhibition of HIV-1 reverse transcriptase: a first step in designing a bifunctional triphosphate.

Dongyuan Piao, Aravind Basavapathruni, Pinar Iyidogan, Guangxiu Dai, Wolfgang Hinz, Adrian S Ray, Eisuke Murakami, Joy Y Feng, Fei You, Ginger E Dutschman, David J Austin, Kathlyn A Parker, Karen S Anderson,

The onset of resistance to approved anti-AIDS drugs by HIV necessitates the search for novel inhibitors of HIV-1 reverse transcriptase (RT). Developing single molecular agents concurrently occupying the nucleoside and nonnucleoside binding sites in RT is an intriguing idea but the proof of concept has so far been elusive. As ... Read more >>

Bioorg. Med. Chem. Lett. (Bioorganic & medicinal chemistry letters)
[2013, 23(5):1511-1518]

Cited: 3 times

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Total synthesis of (±)-bisabosqual A.

Christopher W am Ende, Zhou Zhou, Kathlyn A Parker,

The synthesis of the novel squalene synthase inhibitor, bisabosqual A, was completed in 14 steps (longest linear sequence) from commercially available starting materials. The doubly convergent route employs a tandem 5-exo, 6-exo radical cyclization as the key step. This reaction assembles the fully functionalized tetracyclic core and introduces three stereogenic ... Read more >>

J. Am. Chem. Soc. (Journal of the American Chemical Society)
[2013, 135(2):582-585]

Cited: 6 times

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UVA/B exposure promotes the biosynthesis of dehydroretinol in cultured human keratinocytes.

Juliana I Tafrova, Adriana Pinkas-Sarafova, Erik Stolarzewicz, Kathlyn A Parker, Marcia Simon,

Retinol and its metabolites modulate epithelial differentiation and serve as cellular UV sensors through changes in retinoid status. Of note is the dehydroretinol family which may serve functions distinct from parental retinol. This study focuses on the metabolism of this family and its potential participation in the response of normal ... Read more >>

Mol. Cell. Biochem. (Molecular and cellular biochemistry)
[2012, 364(1-2):351-361]

Cited: 5 times

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Asymmetric induction in 8π electrocyclizations. Design of a removable chiral auxiliary.

Keunsoo Kim, Joseph W Lauher, Kathlyn A Parker,

The pseudo C(2) symmetric trans diphenyl oxazoline group acts as an effective chiral auxiliary in the 8π, 6π tandem electrocyclization of a substituted tetraene 1-carboxylic acid. Assignment of absolute stereochemistry to the [4.2.0] bicyclooctadiene product supports a model in which both s-cis and s-trans conformations favor the transition states with ... Read more >>

Org. Lett. (Organic letters)
[2012, 14(1):138-141]

Cited: 2 times

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Total synthesis of the potent androgen receptor antagonist (-)-arabilin: a strategic, biomimetic [1,7]-hydrogen shift.

Hee Nam Lim, Kathlyn A Parker,

The first total synthesis of (-)-arabilin, a Streptomyces metabolite that inhibits hormone activation of the androgen receptor, has been completed. The key step, a [1,7]-hydrogen shift, establishes the enol ether-containing skipped-tetraene substructure. This nonenzymatic pericyclic reaction is considered to be biomimetic. ... Read more >>

J. Am. Chem. Soc. (Journal of the American Chemical Society)
[2011, 133(50):20149-20151]

Cited: 6 times

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A formal synthesis of (-)-englerin A by relay ring closing metathesis and transannular etherification.

Jungyong Lee, Kathlyn A Parker,

A bicyclization approach to englerin A has culminated in a formal asymmetric total synthesis. Key transformations in the 10-step sequence are a regiospecific epoxide opening and a relay ene-yne-ene metathesis that converts linear substrates specifically to Δ(4,6)-guaiadiene-9,10 diol derivatives. Regiospecific functionalization of the diene moiety installs the oxygen bridge required ... Read more >>

Org. Lett. (Organic letters)
[2012, 14(11):2682-2685]

Cited: 13 times

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Convergent Synthesis of 2H-Chromenes - a Formal [3+3] Cycloaddition by a One-pot, Three-Step Cascade.

Kathlyn A Parker, Thomas L Mindt,

In cases in which the palladium-catalyzed coupling of a bromoquinone with a vinyl stannane affords a vinyl quinone that enolizes, the resulting ortho-quinone methide undergoes an oxa-6π electrocyclization. Enolization is promoted by the presence of a polar additive. The net conversion is a formal [3+3] cycloaddition that gives 2H-chromenes. Because ... Read more >>

Tetrahedron (Tetrahedron)
[2011, 67(51):9779-9786]

Cited: 1 time

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Antibacterial studies of cationic polymers with alternating, random, and uniform backbones.

Airong Song, Stephen G Walker, Kathlyn A Parker, Nicole S Sampson,

Antibacterial polymers have potential as pharmaceuticals and as coatings for implantation devices. The design of these materials will be optimized when we have a complete understanding of the structural features that impart activity toward target organisms and those that are benign with respect to the mammalian host. In this work, ... Read more >>

ACS Chem. Biol. (ACS chemical biology)
[2011, 6(6):590-599]

Cited: 19 times

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Cyclic alternating ring-opening metathesis polymerization (CAROMP). Rapid access to functionalized cyclic polymers.

Airong Song, Kathlyn A Parker, Nicole S Sampson,

Catalysis of alternating ROMP with (H(2)IMes)Cl(2)Ru=CHPh(OiPr), the second generation Hoveyda-Grubbs catalyst, provided an entirely cyclic alternating polymer. Conditions for the cyclic AROMP were used to prepare a polymer in which one of the repeat units bore a primary alkyl chloride that was used for further elaboration. ... Read more >>

Org. Lett. (Organic letters)
[2010, 12(17):3729-3731]

Cited: 7 times

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Scope of the ring-opening metathesis polymerization (ROMP) reaction of 1-substituted cyclobutenes.

Airong Song, Jae Chul Lee, Kathlyn A Parker, Nicole S Sampson,

The reactivities of a series of 1-substituted cyclobutene derivatives (carboxylate esters, carboxamides, and carbinol esters) were investigated as substrates for ring-opening metathesis polymerization (ROMP) with [(H(2)IMes)(3-Br-pyridine)(2)(Cl)(2)Ru=CHPh]. Both the secondary amides of 1-cyclobutenecarboxylic acid and the esters of 1-cyclobutene-1-methanol undergo polymerization. The secondary amides provide translationally invariant polymers (E-olefins). Although the ... Read more >>

J. Am. Chem. Soc. (Journal of the American Chemical Society)
[2010, 132(30):10513-10520]

Cited: 7 times

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Structures of the phosphorylated and VO(3)-bound 2H-phosphatase domain of Sts-2.

Yunting Chen, Jean Jakoncic, Kathlyn A Parker, Nick Carpino, Nicolas Nassar,

The C-terminal domain of the suppressor of T cell receptor (TCR) signaling 1 and 2 (Sts-1 and -2) proteins has homology to the 2H-phosphatase family of enzymes. The phosphatase activity of the correspondent Sts-1 domain, Sts-1(PGM), is key for its ability to negatively regulate the signaling of membrane-bound receptors including ... Read more >>

Biochemistry (Biochemistry)
[2009, 48(34):8129-8135]

Cited: 9 times

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Functional group compatibility. Propargyl alcohol reduction in the presence of a vinyl iodide.

Richard W Denton, Kathlyn A Parker,

Vinyl iodides are stable to the reduction of propargyl alcohols to cis allylic alcohols by hydrogen over Pd/CaCO(3) in hexane. They are also stable to the reduction of propargyl alcohols to saturated alcohols by hydrogen over Crabtree's iridium catalyst in CH(2)Cl(2). ... Read more >>

Org. Lett. (Organic letters)
[2009, 11(13):2722-2723]

Cited: 2 times

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Synthesis of copolymers by alternating ROMP (AROMP).

Airong Song, Kathlyn A Parker, Nicole S Sampson,

The alternating polymerization of cyclobutene 1-carboxylic esters and cyclohexene derivatives with the precatalyst [(H(2)IMes)(3-Br-pyr)(2)Cl(2)Ru=CHPh] is described. This reaction is synthetically accessible and provides (AB)(n) heteropolymers with an alternating backbone and alternating functionality. The regiocontrol of heteropolymer formation derives from the inability of the cyclobutene ester and cyclohexene monomers to undergo ... Read more >>

J. Am. Chem. Soc. (Journal of the American Chemical Society)
[2009, 131(10):3444-3445]

Cited: 21 times

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A relay ring-closing metathesis synthesis of dihydrooxasilines, precursors of (Z)-iodo olefins.

Qiuzhe Xie, Richard W Denton, Kathlyn A Parker,

A convenient Grubbs II metathesis provides dihydrooxasilines by relay RCM (RRCM). Dihydrooxasilines undergo ring opening to give Z-vinyl silanes. These can then be converted to Z-vinyl iodides. This sequence provides a short, high yield, and convenient route to trisubstituted Z-vinyl iodides, useful intermediates for the preparation of polypropionate antibiotics. ... Read more >>

Org. Lett. (Organic letters)
[2008, 10(23):5345-5348]

Cited: 8 times

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Asymmetric catalysis route to anti,anti stereotriads, illustrated by applications.

Kathlyn A Parker, Qiuzhe Xie,

A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" ... Read more >>

Org. Lett. (Organic letters)
[2008, 10(7):1349-1352]

Cited: 2 times

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Short synthesis of the C1-C14 stretch of discodermolide from building blocks prepared by asymmetric catalysis.

Huanyan Cao, Kathlyn A Parker,

A convergent and stereoselective synthesis of the C1-C14 stretch of (+)-discodermolide demonstrates the utility of the "asymmetric catalysis approach" to complex polypropionates. The preparation of this complex synthon requires 15 steps in the longest linear sequence and 19 steps total from inexpensive materials. ... Read more >>

Org. Lett. (Organic letters)
[2008, 10(7):1353-1356]

Cited: 1 time

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Deconstruction-reconstruction strategy for accessing valuable polyketides. Preparation of the C15-C24 stereopentad of discodermolide.

Kathlyn A Parker, Peng Wang,

An advanced, known intermediate for discodermolide synthesis was prepared by an efficient sequence from the readily available fermentation product oleandomycin. The scheme makes use of a new method for the direct cleavage of aminoglycosides, a critical double-bond isomerization, and a selective protection of two of three hydroxyl groups in a ... Read more >>

Org. Lett. (Organic letters)
[2007, 9(23):4793-4796]

Cited: 2 times

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Scalable, catalytic asymmetric synthesis of syn, anti stereotriad building blocks for polypropionate antibiotics.

Kathlyn A Parker, Huanyan Cao,

[reaction: see text] Asymmetric catalysis and chirality transfer by the 2,3-Wittig rearrangement were combined to provide a syn, anti stereotriad-containing olefinic alcohol in five steps from inexpensive starting materials. Development of this compound, a versatile intermediate for polypropionate synthesis, gave known building blocks for discodermolide. ... Read more >>

Org. Lett. (Organic letters)
[2006, 8(16):3541-3544]

Cited: 0 times

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