Gouthami Pashikanti

Design, synthesis, and preliminary in vitro assessment of 3-fluoro-5-aminolevulinic acid as a potential glioma imaging agent

Gouthami Pashikanti

Regioselective Synthesis of 1,2,3-Trisubstituted Pyrroles via Addition–Cyclization of Crotonate-Derived Sulfonium Salts with a Carboxylic Acid and an Amine

Lahu N. Chavan, Gouthami Pashikanti, Mark M. Goodman, Lanny S. Liebeskind

High Resolution Image Download MS PowerPoint Slide A sequential addition-cyclization reaction between carboxylic acids, crotonate sulfonium salts, and amines has been developed for the construction of 1,2,3-trisubstituted pyrroles. The reaction involves regioselective addition of crotonate sulfonium salts directly to in situ -activated …

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Rotamer-Controlled Self-Immolative Linkers Enable Tunable Release of Neurosteroid Oxime Prodrugs

Aletta E. van der Westhuyzen, Luke Hodson, Gouthami Pashikanti, Russell G. Fritzemeier et autres

High Resolution Image Download MS PowerPoint Slide In this work we present a modular prodrug strategy for the controlled release of neurosteroid oximes, exemplified through new synthetic routes for both progesterone and allopregnanolone derivatives. By systematically modifying the self-immolative linker with steric, …

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Rapid and Scalable Synthesis of Oxazoles Directly from Carboxylic Acids

Lahu N. Chavan, Gouthami Pashikanti, Mark M. Goodman, Lanny S. Liebeskind

High Resolution Image Download MS PowerPoint Slide A highly efficient and expedient method for the synthesis of 4,5-disubstituted oxazoles has been developed directly from carboxylic acids, employing a stoichiometric amount of the easy-to-access and stable triflylpyridinium reagent. The overall transformation proceeds through …

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Mild and Chemoselective Triethylsilane-Mediated Debenzylation for Phosphate Synthesis

Luke Hodson, Paul Joseph Tholath, Leon Jacobs, Nicole Pribut et autres

The synthetic utility of tetrabenzyl pyrophosphate for achieving chemoselective phosphorylation of phenols, as well as primary, secondary, and tertiary alcohols, is reported here. Additionally, we introduce a rapid, mild, and chemoselective debenzylation procedure, enabling access to phosphates in the presence of redox …

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Synthetic Efforts toward the Synthesis of a Fluorinated Analog of 5-Aminolevulinic Acid: Practical Synthesis of Racemic and Enantiomerically Defined 3-Fluoro-5-aminolevulinic Acid

Gouthami Pashikanti, Lahu N. Chavan, Lanny S. Liebeskind, Mark M. Goodman

In 2017, the FDA authorized 5-aminolevulinic acid (5-ALA) for intraoperative optical imaging of suspected high-grade gliomas. This was the first authorized optical imaging agent for brain tumor surgery to enhance the visualization of malignant tissue. Herein we report the synthesis of a …

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Synthesis, Radiolabeling, and Biological Evaluation of the trans-Stereoisomers of 1-Amino-3-(fluoro-18F)-4-fluorocyclopentane-1-carboxylic Acid as PET Imaging Agents

Thomas C. Pickel, Gouthami Pashikanti, Ronald J. Voll, Weiping Yu et autres

The enantiomeric non-natural cyclic amino acids (3 R,4 R )-1-amino-3-fluoro-4-(fluoro- 18 F)cyclopentane-1-carboxylic acid and (3 S,4 S )-1-amino-3-fluoro-4-(fluoro- 18 F)cyclopentane-1-carboxylic acid ( [ 18 F]5 ) have been prepared as a racemic mixture in 1.3% decay corrected radiochemical yield and in greater …

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Rapid and one-pot synthesis of tri- to tetradeca-deutero nicotines

Gouthami Pashikanti, Gadela Karteek Goud, Prathama S. Mainkar, S. Chandrasekhar

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Syntheses of 2-Aroyl Benzofurans through Cascade Annulation on Arynes

Gouthami Pashikanti, Lahu N. Chavan, Rambabu Chegondi, S. Chandrasekhar

The highly efficient and expedient route for the syntheses of 2-aroyl benzofurans has been developed via the cascade [2+2] followed by a [4+1] annulation on arynes. The overall transformation proceeded through the formation of ortho-quinone methide by the insertion of transient aryne …

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CCDC 1589669: Experimental Crystal Structure Determination

Gouthami Pashikanti, Lahu N. Chavan, Rambabu Chegondi, S. Chandrasekhar

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, …

Formal Total Synthesis of (±)-Cephalotaxine andCongeners via Aryne Insertion Reaction

Gouthami Pashikanti, Rambabu Chegondi, S. Chandrasekhar

Formal Total Synthesis of (±)-Cephalotaxine and Congeners via Aryne Insertion Reaction

Gouthami Pashikanti, Rambabu Chegondi, S. Chandrasekhar

The formal total synthesis of pentacyclic core alkaloid, (±)-cephalotaxine is achieved in nine steps from known 2-allylpyrrolidine-2-carboxaldehyde using aryne insertion reaction as a key step in 10% overall yield. The developed novel strategy enabled easy access to cephalotaxine congeners.

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