Chapman, Lauren M.; Beck, Jordan C.; Lacker, Caitlin R.; Wu, Linglin; Reisman, Sarah E. published the artcile< Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B>, Formula: C19H34O2, the main research area is enantioselective synthesis psiguadial B Wolff rearrangement asym ketene trapping; aminoquinolinamide enantioenriched synthesis; ortho quinone methide hetero Diels Alder psiguadial B synthesis; Prins cyclization psiguadial B synthesis; Norrish Yang cyclization psiguadial B synthesis; ring closing metathesis psiguadial B synthesis; intramol arylation psiguadial B synthesis.
(+)-Psiguadial B is a diformyl phloroglucinol meroterpenoid that exhibits antiproliferative activity against the HepG2 human hepatoma cancer cell line. This full account details the evolution of a strategy that culminated in the first enantioselective total synthesis of (+)-psiguadial B. A key feature of the synthesis is the construction of the trans-cyclobutane motif by a Wolff rearrangement with in situ catalytic, asym. trapping of the ketene. An investigation of the substrate scope of this method to prepare enantioenriched 8-aminoquinolinamides is disclosed. Three routes toward (+)-psiguadial B were evaluated that featured the following key steps: (1) an ortho-quinone methide hetero-Diels-Alder cycloaddition to prepare the chroman framework, (2) a Prins cyclization to form the bridging bicyclo[4.3.1]decane system, and (3) a modified Norrish-Yang cyclization to generate the chroman. Ultimately, the successful strategy employed a ring-closing metathesis to form the seven-membered ring and an intramol. O-arylation reaction to complete the polycyclic framework of the natural product.
Journal of Organic Chemistry published new progress about Addition reaction, stereoselective (tandem photochem. Wolff rearrangement/enantioselective ketene addition). 112-63-0 belongs to class esters-buliding-blocks, and the molecular formula is C19H34O2, Formula: C19H34O2.
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics