{"title":"Intramolecular Diels-Alder Reaction of Benzo-Tethered Dienyl Cinnamates: Synthesis of the Tricyclic Core of Morusalisin A.","authors":"Poramate Songthammawat, Kasam Poonswat, Pisit Nithijarasrawee, Poonsakdi Ploypradith, Somsak Ruchirawat","doi":"10.1002/asia.202500258","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, a three-step general strategy featuring a thermal intramolecular Diels-Alder (IMDA) reaction to prepare the tricyclic 9-methyl-7-aryl-tetrahydro-6H-benzo[c]chromen-6-one core of morusalisin A is reported. This developed chemistry is applicable to the synthesis of a variety of tricycles, including 9-silyloxy and 9-phenyl-7-aryl-tetrahydro-6H-benzo[c]chromen-6-ones. In addition, a one-pot dehydration/IMDA procedure was demonstrated. The positioning of substituents on the aryldiene moiety played a significant role in governing the endo/exo selectivity, while the overall yield and reaction rate were affected by the electronic properties of both cinnamates and aryldienes. Functional group manipulations of the resulting cycloadducts were performed to furnish synthetically useful derivatives.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202500258"},"PeriodicalIF":3.5000,"publicationDate":"2025-03-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202500258","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
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Abstract
Herein, a three-step general strategy featuring a thermal intramolecular Diels-Alder (IMDA) reaction to prepare the tricyclic 9-methyl-7-aryl-tetrahydro-6H-benzo[c]chromen-6-one core of morusalisin A is reported. This developed chemistry is applicable to the synthesis of a variety of tricycles, including 9-silyloxy and 9-phenyl-7-aryl-tetrahydro-6H-benzo[c]chromen-6-ones. In addition, a one-pot dehydration/IMDA procedure was demonstrated. The positioning of substituents on the aryldiene moiety played a significant role in governing the endo/exo selectivity, while the overall yield and reaction rate were affected by the electronic properties of both cinnamates and aryldienes. Functional group manipulations of the resulting cycloadducts were performed to furnish synthetically useful derivatives.
期刊介绍：
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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