Total synthesis of kadsurenone and its analogs

A Streamlined Synthesis of 2,3‐Dihydrobenzofurans via the ortho‐Quinone Methides Generated from 2‐Alkyl‐Substituted Phenols

“…Additionally, 2,3‐dihydrobenzofurans have also been developed for the treatment of traumatic and ischemic central nervous system injury 3. Thus, the synthesis of 2,3‐dihydrobenzofurans has received extensive attention in the past decades and various efficient methodologies for the construction of 2,3‐dihydrobenzofurans have been developed, including electrocyclization,4 radical cyclization,5 anionic cyclization,6 transition metal‐catalyzed cyclization,7 cycloaddition,8 biomimetic coupling,9 Lewis acid‐promoted reactions 10. Although significant progress has been made in the synthesis of 2,3‐dihydrobenzofurans, most of these existing routes have several drawbacks involving poor chemo‐ and/or diastereoselectivities, unsatisfactory yields, tedious processes and harsh reaction conditions, prohibiting their wider application.…”

The Stereoselective Synthesis of Neolignans

“…The Schmid rearrangement was first used by Gottlieb and Aiba for the synthesis of licarin B (31), 58 an immunosuppressive neolignan, 59 and later by Ponpipom et al for the construction of dihydrobenzofuran 32, an intermediate in the synthesis of the PAF-anatagonist kadsurenone (chapter 3). 60 The same key reaction was also used for the preparation of kadsurenin M (33) 61 and a bicyclo[3.2.1]octane neolignan (chapter 7). 62 The yields of the desired rearrangement products were ca.…”

“…25%) etherification reaction under Mitsunobu conditions. 60 Better yields of similar ethers have been accomplished in the reaction of 3,4-dimethoxycinnamyl chloride with the sodium salt of vanillin in DMF (60%). 61 Chalcone epoxides, easily prepared by nucleophilic epoxidation, rearranges upon treatment with Lewis acids to 31 8,8¢-neolignan.…”

Progress in the Development of Platelet‐Activating Factor Receptor (PAFr) Antagonists and Applications in the Treatment of Inflammatory Diseases

“…Notably, Popinom et al. prepared molecule 9 in only three steps from allyloxyphenol and 3,4‐dimethoxycinnamyl alcohol by developing a novel pericyclic cascade reaction . Over a decade later, a biomimetic synthesis of this natural product was reported …”