Dayaker, Gandrath’s team published research in Chemistry – A European Journal in 20 | CAS: 19444-84-9

Chemistry – A European Journal published new progress about 19444-84-9. 19444-84-9 belongs to tetrahydrofurans, auxiliary class Tetrahydrofuran,Ester,Alcohol, name is 3-Hydroxydihydrofuran-2(3H)-one, and the molecular formula is C4H6O3, Name: 3-Hydroxydihydrofuran-2(3H)-one.

Dayaker, Gandrath published the artcileA Versatile and Stereocontrolled Total Synthesis of Dihydroxylated Docosatrienes Containing a Conjugated E,E,Z-Triene, Name: 3-Hydroxydihydrofuran-2(3H)-one, the publication is Chemistry – A European Journal (2014), 20(10), 2879-2887, database is CAplus and MEDLINE.

A versatile strategy featuring a Colvin rearrangement, hydrozirconation, a Sonogashira cross-coupling reaction and a (Z)-selective Wittig olefination, was successfully developed for the construction of a conjugated E,E,Z-triene subunit, flanked on both sides by two (Z)-allylic hydroxy-groups. This chem. pattern is found in many endogenous lipid metabolites such as maresin 1 (MaR1), neuroprotectin D1 (NPD1) and its aspirin triggered-isomer AT-NPD1, which not only counter-regulate inflammation but also actively orchestrate (at nanomolar doses) the resolution and termination program of acute inflammation while promoting wound healing, return to homeostasis and neuroprotection. Unlike previous approaches, the advantages of the present strategy are obvious, as it allows a modification of a nonpolar tail, the carboxylated head or both ends of the mol. without repeating the whole synthetic sequence (about 26-34 steps according to the literature). Thus, the first total synthesis of NPD1 Me ester epimer (which can also be considered as an enantiomer of AT-NPD1) and its n-3 docosapentaenoic acid derived analog were achieved from a highly functionalized and late advanced pivotal intermediate. This innovative route may be easily adapted to gain access to other dihydroxylated metabolites and analogs of polyunsaturated fatty acids containing a conjugated E,E,Z-triene subunit. Different epimers/diastereoisomers may be obtained by purchasing the suitable optically pure (S)- and/or (R)-1,2,4-butanetriol derivatives as a chiral pool for both stereogenic centers. The tilte compound thus formed included (4Z,7Z,10S,11E,13E,15Z,17S,19Z)-10,17-dihydroxy-4,7,11,13,15,19-docosahexaenoic acid Me ester (I) which is an epimer of neuroprotectin-D1 Me ester and (7Z,10S,11E,13E,15Z,17S,19Z)-10,17-Dihydroxy-7,11,13,15,19-docosapentaenoic acid Et ester which is an omega-3 docosapentaenoic acid (n-3 DPA) analog.

Chemistry – A European Journal published new progress about 19444-84-9. 19444-84-9 belongs to tetrahydrofurans, auxiliary class Tetrahydrofuran,Ester,Alcohol, name is 3-Hydroxydihydrofuran-2(3H)-one, and the molecular formula is C4H6O3, Name: 3-Hydroxydihydrofuran-2(3H)-one.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem