First total synthesis of Papilistatin

Abstract

Papilistatin has been isolated recently and found to have good anticancer and antibacterial activity. Papilistatin is a unique phenanthrene-1,10-dicarboxylic acid. The first total synthesis of papilistatin is described here with radical cyclisation as the key step.

Progress on the Synthesis and Applications of Aminals: Scaffolds for Molecular Diversity

“…Under blue LED irradiation, the polymeric graphite carbon nitride (g-C3N4) provided a promising four-component reaction for the synthesis of spiro-aminals from simple amines, ketones, amino acids, and aldehydes. Miyake et al 54 developed a photocatalytic reaction of di-tert-butyl azodicarboxylate (105a) with nitrogen-containing benzoheterocycles (104), such as 1,2,3,4-tetrahydroquinolines and indolines to achieve aminals derivatives (106). The reaction is promoted by a Ir-photocalyst and irradiation with a 14W white LED in N-methyl-2pyrrolidone (NMP) at room temperature (Scheme 21).…”

“…Additionally, the authors were able to access alternative sixmembered benzocyclic amines, such as 1,2,3,4tetrahydroquinoxaline (106e), 3,4-dihydro-2H-1,4benzoxazine (106f), 3,4-dihydro-2H-benzo-1,4-thiazine (106h), and the seven-membered benzocyclic amine (106g) in moderate yields. Ther use of azodicarboxylate esters (104) for the photocatalytic synthesis of aminals was also exploited by Papadopoulos et al 55 and Berenguer et al 56 Scheme 21 C-H amination of nitrogen-containing benzoheterocycles mediated by visible-light-photoredox catalysts.…”

A Fully Palladium‐Mediated Construction of Phenanthrenes and Naphthoxindoles

“…[5] Wang and co-workers also recently reported an elegant total synthesis of papilistatin that involved the radical cyclization of a bromostilbene intermediate with a modest yield (30 %). [6] In contrast, until now, cyclization of stilbenes by direct C-H arylation has mostly been overlooked. [7] In the context of a medicinal chemistry project, we wish to report our latest investigations, which ultimately led to the preparation of naphthoxindoles E through a fully palladium-catalyzed, three-step process, as illustrated in Scheme 1.…”

Design, Synthesis, and Bioactivity of Chalcone Derivatives Containing Indanone

“…To name only a few, 1-methoxy-6-methyl-3-oxo-2,3-dihydro-1 H -4-aldehyde ( I ) and pterosin B ( II ) extracted from marine cyanobacteria and Pteris ensiformis are found to contain indanone structural units, , as shown in Figure . Indanones have antibacterial, antiviral, anti-Alzheimer’s disease, antitumor, and other biological activities . Some of them have been used in clinical practice.…”

“…Indanones have antibacterial, 19 antiviral, 20 anti-Alzheimer’s disease, 21 antitumor, 22 and other biological activities. 23 Some of them have been used in clinical practice. For example, donepezil ( III ), 24 an acetylcholinesterase inhibitor, has been approved by the United States Food and Drug Administration for the treatment of Alzheimer’s disease.…”