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. 2024 Jan 12;26(1):18-21.
doi: 10.1021/acs.orglett.3c03434. Epub 2023 Dec 28.

Synthesis of Functionalized Hexahydrocarbazoles by Beckmann Elimination and Nucleophile-Intercepted Beckmann Fragmentation

Dhiman Saha  1 , Zachary Protich  1 , Jimmy Wu  1
Affiliations

Synthesis of Functionalized Hexahydrocarbazoles by Beckmann Elimination and Nucleophile-Intercepted Beckmann Fragmentation

Dhiman Saha et al. Org Lett. .

Abstract

The Beckmann elimination and nucleophile-intercepted Beckmann fragmentation (NuBFr) of oximes starting from regioisomeric indolinyl bicyclic ketones lead to products that are subjected to further synthetic manipulations and ultimately result in the stereospecific formation of densely functionalized hexahydrocarbazoles. The Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of a key alkenyl bromide intermediate with various boronic acids gives arylated products.

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Conflict of interest statement

The authors declare no competing financial interests.

Figures

Figure 1.
Figure 1.
Representative hexahydrocarbazoles in Nature.
Figure 2.
Figure 2.
NuBFr mechanism and current work.
Scheme 1.
Scheme 1.
Proposed Mechanism for the Formation of 8.
See this image and copyright information in PMC

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