Intramolecular Diels-Alder Reaction of Benzo-Tethered Dienyl Cinnamates: Synthesis of the Tricyclic Core of Morusalisin A

IF 3.3 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - An Asian Journal Pub Date : 2025-03-08 DOI:10.1002/asia.202500258
Dr. Poramate Songthammawat, Kasam Poonswat, Pisit Nithijarasrawee, Dr. Poonsakdi Ploypradith, Prof. Dr. Somsak Ruchirawat
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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.

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苯并系二烯基肉桂酸酯的分子内diel - alder反应:肉桂素A三环核心的合成。
本文报道了采用分子内Diels-Alder (IMDA)热反应三步制得morusalisin a三环9-甲基-7-芳基-四氢- 6h -苯并[c]铬-6- 1核的一般策略。这一发展的化学反应适用于合成各种三环,包括9-硅氧基和9-苯基-7-芳基-四氢- 6h -苯并[c]铬-6-酮。此外,还演示了一锅脱水/IMDA程序。取代基在芳基二烯上的位置对反应的内/外选择性起重要作用,而肉桂酸酯和芳基二烯的电子性质对反应的总收率和反应速率均有影响。对所得到的环加合物进行官能团操作以获得合成上有用的衍生物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
Chemistry - An Asian Journal
Chemistry - An Asian Journal 化学-化学综合
CiteScore
7.00
自引率
2.40%
发文量
535
审稿时长
1.3 months
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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