34425-64-4Relevant articles and documents
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Karrer,Lichtenstein
, p. 795 (1928)
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Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B
Chapman, Lauren M.,Beck, Jordan C.,Lacker, Caitlin R.,Wu, Linglin,Reisman, Sarah E.
supporting information, p. 6066 - 6085 (2018/05/15)
(+)-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, asymmetric 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 intramolecular O-arylation reaction to complete the polycyclic framework of the natural product.
Reactions of carbanions with 1,3-benzodioxin-4-ones: Facile routes to flavones, aurones, and acyl phloroglucinols
Kraus, George A.,Wie, Jingqiang,Thite, Aniket
experimental part, p. 2427 - 2431 (2009/04/06)
Two 1,3-benzodioxin-4-ones react with enolates, acetylides and aryllithium reagents to afford adducts that were converted into flavones, aurones, and an acyl phloroglucinol. Georg Thieme Verlag Stuttgart.
