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Showing papers by "Louis J. Farrugia published in 2015"


Journal ArticleDOI
TL;DR: In this article, the electrostatic potential mapped on Hirshfeld surfaces generated for these crystal forms of sulfamethizole, a sulfonamide antibiotic, was analyzed in order to examine the possible conformational preferences of the molecule in various ionic states and supramolecular environments.
Abstract: Intramolecular S···O chalcogen bonding and its potential to lock molecular conformation have been examined in the crystal forms of sulfamethizole, a sulfonamide antibiotic. Molecular complexes of sulfamethizole, including salts and cocrystal, have been synthesized, and their crystal structures were analyzed in order to examine the possible conformational preferences of the molecule in various ionic states and supramolecular environments (neutral/cocrystal, anionic salt, and cationic salt forms). The electrostatic potential mapped on Hirshfeld surfaces generated for these crystal forms provides insights into the possible binding modes of the drug in different environments. Further, the observed conformation locking feature has been rationalized in terms of the experimental charge density features of the intramolecular S···O chalcogen bonding in sulfamethizole. The study quantitatively illustrates and rationalizes an intriguing case of a local minimum of molecular conformation being exclusively preferred ov...

53 citations


Journal ArticleDOI
TL;DR: Synthetically relevant polycyclic building blocks featuring rings of various sizes and heteroatoms have been synthesized in high yield using this mild acid-catalyzed reaction of electron-deficient ynenones.
Abstract: Chloroacetic acid promotes an efficient and diastereoselective intramolecular cascade reaction of electron-deficient ynenones to deliver products featuring a 2,3,5-trisubstituted furan bearing a fused cyclopropyl substituent at the 5-position. Synthetically relevant polycyclic building blocks featuring rings of various sizes and heteroatoms have been synthesized in high yield using this mild acid-catalyzed reaction.

36 citations


Journal ArticleDOI
TL;DR: In this article, the catalytic activity of RuCl2(η6-C6H6) with chiral aroylthiourea ligands yielded pseudo-octahedral half-sandwich "piano-stool" complexes.

26 citations


Journal ArticleDOI
TL;DR: Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophicaltins E and F are the same compound.
Abstract: Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products.

7 citations


Journal ArticleDOI
TL;DR: In this article, the authors used the reaction of [Ni(H 2 O) 6 ](NO 3 ) 2 with NH 3(g) at room temperature to create macro-crystals with diameters up to ca. 0.05mm.

4 citations


Journal ArticleDOI
TL;DR: The synthesis of compound (I) is based on the proposed structure of natural product sclerophytin F as mentioned in this paper, which is a compound based on a mixture of SCL and SCL.
Abstract: The synthesis of compound (I) is based on the proposed structure of natural product sclerophytin F.

Journal ArticleDOI
TL;DR: A high-yielding, diastereoselective intramolecular reaction cascade reaction is developed creating three new bonds in a single step, thus providing 2,3,5-substituted furans bearing a ring fused cyclopropyl substituent.
Abstract: A high-yielding, diastereoselective intramolecular reaction cascade reaction is developed creating three new bonds in a single step, thus providing 2,3,5-substituted furans bearing a ring fused cyclopropyl substituent.

Journal ArticleDOI
TL;DR: In this article, a one-pot four-step multi-reaction process involving a thermal Overman rearrangement, a tandem metathesis reaction, and a Diels-Alder reaction is developed for the diastereoselective synthesis of aminobicyclononanes and -decanes with up to five stereogenic centers.
Abstract: A one-pot four-step multi-reaction process involving a thermal Overman rearrangement, a tandem metathesis reaction, and a Diels—Alder reaction is developed for the diastereoselective synthesis of aminobicyclononanes and -decanes with up to five stereogenic centers.