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DOI: 10.1055/a-2384-6736
Design and Synthesis of Out/Out, Out/In, and In/In Epoxides in Polycyclic Cage Frameworks
M.S. thank the University Grants Commission (UGC), New Delhi for the award of a research fellowship.
Abstract
We report a useful synthetic approach to assemble in/in epoxide, in/out epoxide, and out/out epoxide in cage systems using the Corey–Chaykovsky reaction and the Peterson olefination as key steps. In this regard, a variety of pentacycloundecane (PCUD) based cage compounds containing oxirane rings with diverse stereochemical disposition were synthesized via a simple synthetic sequence. Five cage diones were used for this purpose, and the starting cage diones were prepared with easily accessible starting materials such as 1,4-hydroquinone derivatives and cyclopentadiene. Here, we have used the Diels–Alder (DA) reaction, a [2+2] photocycloaddition, the Corey–Chaykovsky reaction, and the Peterson olefination as crucial steps to prepare the target molecules.
Key words
Diels–Alder reaction - photocycloaddition - cage compounds - PCUD - Peterson olefination - Corey–Chaykovsky reaction - m-CPBA oxidationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2384-6736.
- Supporting Information
Publikationsverlauf
Eingereicht: 02. Juli 2024
Angenommen nach Revision: 12. August 2024
Accepted Manuscript online:
12. August 2024
Artikel online veröffentlicht:
10. September 2024
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