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Synlett 2022; 33(06): 589-583
DOI: 10.1055/s-0041-1737334
DOI: 10.1055/s-0041-1737334
letter
Highly Stereoselective Formation of a Spiro Center by a 1,4-Addition/Elimination Reaction of 3,5-Difluorocyclohexa-2,5-dienones
This work was generously supported by funding from the Research Foundation ITSUU Laboratory.
Abstract
Spirocyclic 3,5-difluorocyclohexa-2,5-dienones possessing a triisopropylsiloxy-containing cyclic ether appendage were synthesized by oxidative dearomatization of the corresponding phenols. By group selectivity in the nucleophilic 1,4-addition/elimination reaction, highly stereoselective formation of the spiro center was successfully achieved. This reaction might provide access to total syntheses of (+)-bisdechlorogeodin and (+)-geodin with complete control of the formation of the spirocyclic structure.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1737334.
- Supporting Information
Publication History
Received: 22 November 2021
Accepted after revision: 29 December 2021
Article published online:
27 January 2022
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References and Notes
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