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In this study, we report the synthesis of chiral \u03c0\u2010conjugated polycycles incorporating a chiral epoxycyclooctadiene moiety. Our synthetic strategy capitalizes on the novel reactions of hetera\u2010buckybowl triselenasumanene (TSS) and is achieved in two\u2010step manner. Firstly, the TSS is regio\u2010selectively transformed into its <jats:italic>ortho<\/jats:italic>\u2010quinone form. Subsequently, the nucleophilic addition reactions of TSS <jats:italic>ortho<\/jats:italic>\u2010quinone by phenylethynides are metal ion\u2010dependent. When utilizing (phenylethynyl)magnesium bromide as the nucleophile, two phenylethynyls are furnished onto the edged benzene ring of TSS. When the nucleophile is (phenylethynyl)lithium, a cascade of nucleophilic addition, intermolecular electron\u2010transfer, ring\u2010opening, and tetradehydro\u2010Diels\u2013Alder (TDDA) reactions occur sequentially in one\u2010pot, ultimately affording chiral \u03c0\u2010conjugated polycycles featuring the epoxycyclooctadiene moiety as an integral part of their backbones. This work represents a step forward in the synthesis of chiral \u03c0\u2010conjugated polycycles using TSS as synthon.<\/jats:p>","DOI":"10.1002\/chem.202303085","type":"journal-article","created":{"date-parts":[[2023,10,25]],"date-time":"2023-10-25T04:53:51Z","timestamp":1698209631000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Transforming Hetera\u2010Buckybowls into Chiral Conjugated Polycycles Incorporating Epoxycyclooctadiene: a Two\u2010Step Approach"],"prefix":"10.1002","volume":"29","author":[{"given":"Xue","family":"Wang","sequence":"first","affiliation":[{"name":"Research Centre for Free Radical Chemistry of Lanzhou University State Key Laboratory of Applied Organic Chemistry Lanzhou University  Tianshui Southern Road 222 Lanzhou Gansu Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinqiang","family":"Hua","sequence":"additional","affiliation":[{"name":"Research 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