English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Plus annual

Presents the access of premium content as premium feature

Premium Content

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools annual

Global: Zendy Free Plan

Global: Zendy Tools monthly

Global: Zendy Plus monthly

The first total synthesis of 5-(1-hydroxy-1-ethyl)-2-isopropyliden-2H-benzofuran-3-one, is reported in its\udracemic and in one of its optically active [(S)-( )] forms. This heterocycle, isolated from Verbesina\udluetzelburgii, is the only known 2-isopropyliden-2H-benzofuran-3-one produced by species of\udVerbesina. The sequence took place in eight steps and 19% overall yield (up to 33% for the chiral form),\udfrom 40-hydroxyacetophenone. It entailed carbonyl group protection as the 1,3-dioxolane and a phenol\udortho formylation, followed by a Williamson etherification with chloroacetone and an organocatalytic\udcross-aldolization, to afford a 2-acetyl-2,3-dihydrobenzofuran-3-ol intermediate. The latter underwent\uda methyl Grignard addition to the carbonyl moiety, followed by selective oxidation of the benzylic\udalcohol and deprotection, resulting in a b-hydroxy diketone derivative. A MsCl-assisted dehydration of\udthe tertiary alcohol, established the isopropylidene motif, whereas the syntheses culminated by chemical\udor enzymatic (carrot, celeriac) selective reductions of the exocyclic carbonyl group.Fil: Kaufman, Teodoro Saúl. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina.Fil: Bracca, Andrea Beatriz Juana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina.Fil: Larghi, Enrique Leandro. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina.Fil: Pergomet, Jorgelina Leonor. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina

First total synthesis of the only known 2-isopropyliden-2H-benzofuran-3-one isolated from V. luetzelburgii