
Gints SmitsLatvian Institute of Organic Synthesis | Latvian IOS
Gints Smits
PhD
About
22
Publications
1,242
Reads
How we measure 'reads'
A 'read' is counted each time someone views a publication summary (such as the title, abstract, and list of authors), clicks on a figure, or views or downloads the full-text. Learn more
246
Citations
Publications
Publications (22)
A fully stereo-divergent Ireland-Claisen rearrangement of achiral lactones has been developed enabling access to all four possible stereoisomers of 3,4-disubstituted piperidines and pyrrolidines. The utility of these building blocks has...
Spider silk is renowned for its exceptional mechanical properties, surpassing those of other natural and many synthetic fibers. Yet, replicating its remarkable properties through synthetic production remains a challenge. The variability in the mechanical properties of synthetic spider silks lacking protective coatings, exacerbated by factors such a...
Classical psychedelics such as psilocybin, lysergic acid diethylamide (LSD), and N,N-dimethyltryptamine (DMT) are showing promising results in clinical trials for a range of psychiatric indications, including depression, anxiety, and substance abuse disorder. These compounds are characterized by broad pharmacological activity profiles, and while th...
A 3-step route toward pyrrolo[1,4]benzodiazepine (PBD) antitumor antibiotic class members oxo-prothracarcin and boseongazepine B has been developed. This methodology also enables preparing oxo-tomaymycin in only 4 linear steps representing the...
Over the past two decades, Julia‐Kocienski olefination has become one of the most powerful and reliable C=C double‐bond construction methods typically furnishing E‐configured alkenes. This review summarizes the scientific literature of the past decade focusing on the key aspects for successful execution of the olefination step. The main stereoselec...
Total syntheses of three pyrrolo[1,4]benzodiazepine anticancer antibiotic family members oxo-prothracarcin, oxo-tomaymycin, and boseongazepine B are described. The total syntheses feature late-stage stereoselective olefination employing modified Julia-Kocienski reagents that can be conveniently prepared in only two steps and allows for a significan...
The stereoselective total synthesis of the proposed structure of a potent serotonin 5-HT1A receptor agonist uncarialin A (1) is described. By employing the readily available meroquinene tert-butyl ester as the chiral synthon, the target structure has been prepared in a six-step linear sequence with a 17% overall yield. In comparison to the sample i...
The isolation of the antitumor antibiotic anthramycin in the 1960s prompted extensive research into pyrrolo[1,4]benzodiazepines (PBD) as potential therapeutics for the treatment of cancers. Since then, nearly 60 PBD natural products have been isolated and evaluated with regard to their biological activity. Synthetic studies and total syntheses have...
A synthetic approach towards the core of a structurally unique cytotoxic indole alkaloid eleganine A has been accomplished for the first time. The synthesis features a stereoselective Ireland-Claisen rearrangement as...
A comprehensive screening of known methods for the synthesis of coumarins was performed in order to obtain a new type of pyrrolobenzodiazepine–coumarin hybrids. A Pechmann condensation turned out to be the method of choice for successful synthesis of the desired hybrid starting from the corresponding phenol derivative and malic acid. Overall, the d...
The first total synthesis of flavesines G and J, natural products exhibiting antiviral activity against hepatitis B virus, is described. A robust, protecting-group-free route starting from commercially available natural product 9-azajulolidine allowed us to obtain the title compounds in a four- and five-step sequence accordingly. Flavesines G and J...
The total synthesis of both the double bond isomers of indolizine alkaloid 8-deoxypumiliotoxin 193H has been accomplished. Both the double bond isomers Z-4 and E-4 induced convulsions and inhibited neuro-muscular activity at a dose of 25 mg/kg after intraperitoneal injection in mice. The lethal dose of Z-4 and E-4 was 100 mg/kg, indicating that 8-d...
A formal total synthesis of pyrrolo[1,4]benzodiazepine (PBD) anticancer antibiotic family member Limazepine E is described. The synthesis features a stereoselective introduction of trisubstituted double bond using novel sterically demanding Julia-Kocienski reagents, allowing significantly reduce the number of linear steps. The potential of the newl...
The electronic and steric properties of tailored Cyclopentadienyl (Cp) ligands are a powerful handle to modulate their catalytic properties of their metal complexes. This requires the individual preparation, purification and storage of each ligand / metal combination. Alternative, ideally in situ complexation protocols would be of high utility. We...
The first total synthesis of usabamycins A and C from inexpensive and readily available amino acids – homoalanine and glycine and featuring a stereoselective Ireland-Claisen rearrangement as well as a novel 7-membered ring formation reaction is described.
The Ireland–Claisen rearrangement of 6-methylene-1,4-oxazepan-2-one-derived boron enolates leads to stereochemically defined, synthetically useful 4-(E)-ethylidene prolines. Detailed computational and experimental studies explain the stereochemical outcome of this transformation and suggest an unusual double-chelated transition state that involves...
A one-step synthesis of pyrrolo[1,4]benzodiazepine dilactams has been developed. The high yielding method involves direct coupling of unprotected anthranilic acids with proline esters. This transformation was successfully applied in the first total syntheses of boseongazepines B and C as well as oxoprothracarcin and limazepine E.
The first total syntheses of limazepines C and D were accomplished from inexpensive and readily available starting materials using an iron pentacarbonyl promoted allylamide – enamide double bond migration as a key step. The obtained limazepine C was found to be unstable and undergoes oxidation to limazepine D.
A stereoselective total synthesis of one diastereomer of 8-deoxypumiliotoxin 193H is described. The concise total synthesis features the use of readily available natural amino acids as the starting materials and the Ireland-Claisen rearrangement as the key stereochemistry controlling step. A stereoselective total synthesis of 8-deoxypumiliotoxin 19...
Stereoselective total syntheses of Limazepine E and Barmumycin, potent, naturally occurring antitumor agents, are described. The total syntheses control the olefin geometry via a highly selective chelation-controlled Ireland-Claisen rearrangement of a seven-membered lactone-derived boron enolate for the synthesis of (E)-4-ethylidene proline, a cruc...