Qureshi, Zafar published the artcileApplication of the Palladium-Catalyzed Norbornene-Assisted Catellani Reaction Towards the Total Synthesis of (+)-Linoxepin and Isolinoxepin, Safety of (R)-Oxiran-2-ylmethanol, the publication is European Journal of Organic Chemistry (2014), 2014(19), 4053-4069, database is CAplus.
The authors’ ongoing effort towards the development of highly selective transition-metal-catalyzed carbon hydrogeb bond (C-H bond) activation processes has led to the expansion of a Catellani reaction. In a Pd0/PdII/PdIV-catalyzed tandem reaction (domino reaction), an aryl iodide, alkyl iodide and tert-Bu acrylate were combined to synthesize a carbon framework of the novel lignan (+)-linoxepin. The enantioselective synthesis highlights the work accomplished in the authors’ group and provides an excellent procedure for a reliable and scalable synthesis of architecturally complex scaffolds. This report outlines the synthetic approaches towards this interesting class of biol. active mols. After a key Catellanireaction/Heck reaction, the synthesis features a Leimeux-Johnson oxidation and a titanium tetrachloride mediated aldol condensation. Finally, a tuneable Mizoroki-Heck reaction was performed to furnish not only the natural product (+)-linoxepin but also its isoform, which we have named isolinoxepin. The synthesis of the target compounds was achieved using 8-[(5-bromo-1,3-benzodioxol-4-yl)methoxy]-3a,4-dihydro-7-(methoxy)naphtho[2,3-c]furan-1(3H)-one as a key intermediate. The title compounds thus formed included (9aR)-9a,10-dihydro-6-methoxy-4H-1,3-benzodioxolo[4,5-c]isobenzofuro[4,5,6-ef][1]benzoxepin-12(9H)-one [(+)-linoxepin] and 10,12b-dihydro-6-methoxy-4H-1,3-benzodioxolo[4,5-c]isobenzofuro[4,5,6-ef][1]benzoxepin-12(9H)-one [racemic isolinoxepin].
European Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Safety of (R)-Oxiran-2-ylmethanol.
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