five

Total Syntheses of Aflavazole and 14-Hydroxyaflavinine

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https://figshare.com/articles/dataset/Total_Syntheses_of_Aflavazole_and_14-Hydroxyaflavinine/4249877
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The first total syntheses of aflavazole (6) and 14-hydroxyaflavinine (8), two sterically congested indole diterpenoids, were accomplished. AlI3-promoted alkyne Prins cyclization was exploited to construct their key structural motifs. An electrocyclization–aromatization sequence assembled the pentasubstituted arene of 6, and a Stille–Migita coupling furnished the tetrasubstituted olefin of 8. The benzylic and allylic C–O bonds were reductively cleaved at the late stage of the syntheses, respectively.
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2016-11-23
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