A palladium catalyzed dicarbonylation of α-iodo-substituted ACPs for the synthesis of carbamoyl substituted indenones has been developed. Two carbonyl groups were incorporated into the product with the cleavage of the proximal C−C bond of the ACPs. A broad range of carbamoyl substituted indenones were efficiently prepared in good to excellent yields.
False identity: The synthesis of a natural product described by Faulkner and co‐workers two decades ago has revealed the need for the revision of some stereochemical assignments. The key steps in this flexible route, which could provide access to stereodefined analogues for biological evaluation, included a Julia coupling, a Suzuki–Miyaura reaction, and Wittig olefination (see scheme; MOM, PMB, and TBS are protecting groups).
A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate.
An efficient and straightforward Lewis-acid-mediated stereoselective (4 + 3)-cyclization of indole-substituted alkylidene malonates and donor−acceptor cyclopropanes has been developed involving the Friedel−Crafts/Michael addition cyclization cascade. This reaction provides a mild and effective method for the construction of synthetically and structurally interesting functionalized cycloheptannelated indoles.
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