78238-02-5Relevant academic research and scientific papers
Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Meroterpenoid (+)-Taondiol
Dethe, Dattatraya H.,Mahapatra, Samarpita,Sau, Susanta Kumar
supporting information, p. 2766 - 2769 (2018/05/22)
The first enantioselective total synthesis of (+)-taondiol, a pentacyclic marine meroterpenoid, has been achieved, which in addition to confirming the structure also established the absolute configuration of the natural product. The notable points in the synthetic route are synthesis of a highly functionalized tricyclic diterpenoid moiety starting from an enantiopure Wieland-Miescher ketone derivative in concise manner via Robinson-type annulation and an elegant hydrogen atom transfer olefin reduction followed by Lewis acid-catalyzed Friedel-Crafts reaction for one-pot C-C and C-O bond formations resulting in construction of the pentacyclic meroterpenoid skeleton.
Optimization of the antioxidant activity of hydroxy-substituted 4-thiaflavanes: A proof-of-concept study
Viglianisi, Caterina,Bartolozzi, Maria Grazia,Pedulli, Gian Franco,Amorati, Riccardo,Menichetti, Stefano
supporting information; experimental part, p. 12396 - 12404 (2011/11/29)
The design and the synthesis of a new family of hydroxy-4-thiaflavanes, in which the reactive phenolic OH is ortho to the sulfur atom of the benzofused oxathiin ring, allowed to prepare antioxidants that show rate constants for the reaction with peroxyl radicals (kinh), and bond dissociation energies (BDE), of the ArO-H group identical to those of α-tocopherol, the main component of vitamin E and the most effective lipophilic antioxidant known in nature. The peculiar conformation of the six-membered heterocyclic ring prevents the formation of an intramolecular hydrogen bond between the OH group and the S atom, while ensuring a good stabilization by electron donation of the phenoxyl radical formed after the reaction with peroxyl radicals. The preparation of these compounds was achieved through an inverse electron demand hetero Diels-Alder reaction of styrenes with o-thioquinones, in turn prepared from accurately designed 1,3-dihydroxy arenes. Properly arranging the substitution pattern on the aromatic ring, as in derivatives 9 and 11, allowed to reach values of kinh up to 4.0× 106 M-1 s -1 and BDE(OH) of 77.2 kcal mol-1. This approach represents an innovative way to obtain highly active antioxidants without using strongly electron donating alkylamino groups which are associated with adverse toxicological profiles. Sulfur makes the difference (again): The stereoelectronic features triggered by the sulfur atom in the benzo-fused six-membered ring of 4-thiaflavanes have been exploited to design a new family of phenolic antioxidants that show an ability to react with peroxyl radicals identical to that of α-tocopherol, the main component of vitamin E and the most potent natural lipophilic antioxidant (see scheme). Copyright
INTRODUCTION OF A HYDROXYL GROUP INTO THE CREOSOL MOLECULE
Kozlova, I. V.,Obol'nikova, E. A.,Chupina, L. N.,Bekker, A. R.,Samokhvalov, G. I.
, p. 296 - 299 (2007/10/02)
The introduction of a hydroxyl group into the molecule of 2-methoxy-4-methylphenol through Rieche formylation and Baeyer-Villiger oxidation was investigated.With dichloromethyl methyl ether meta-formylation of creosol occurs.
