1775-23-1Relevant academic research and scientific papers
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.
, 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.
Synthesis of pyrazoles through catalyst-free cycloaddition of diazo compounds to alkynes
Vuluga, Daniela,Legros, Julien,Crousse, Benoit,Bonnet-Delpon, Daniele
supporting information; experimental part, p. 156 - 159 (2010/04/22)
The synthesis of pyrazoles via 1,3-dipolar cycloaddition of diazo compounds to alkynes proceeds easily by heating. With α-diazocarbonyl substrates the reactions are conducted under solvent-free conditions affording the pyrazole products in high yields wit
A Simple Procedure for Preparation of α-Diazocarbonyl Compounds
Rao, Y. Koteswar,Nagarajan, M.
, p. 735 - 737 (2007/10/02)
The use of 1,8-diazabicycloundec-7-ene as a base in Regitz reaction leads to improved yields of α-diazocarbonyl compounds in much shorter time (15 min).
