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Synlett 2022; 33(15): 1473-1480
DOI: 10.1055/s-0041-1737966
DOI: 10.1055/s-0041-1737966
synpacts
Ring Forming Approaches to para-Quinones: Toward a General Diels–Alder Disconnection
This work was supported by an Australian Research Council Discovery Early Career Award for C.G.N. (DE180100462). Financial support from the University of Adelaide, Australia and the University of Georgia, USA is gratefully acknowledged.
Abstract
para-Quinones feature extensively as targets and/or intermediates throughout a number of chemical and biological subdisciplines, highlighting the importance of efficient preparative methods. This Synpacts article provides an overview of ring forming approaches to para-hydroquinones and para-benzoquinones, concluding with our recent contribution concerning the development of 2,5-bis(tert-butyldimethylsilyloxy)furans as vicinal bisketene equivalents in the Diels–Alder reaction.
1 Introduction
2 Ring Forming Approaches to para-Quinones
2.1 Hauser–Kraus Annulation
2.2 Moore–Liebeskind Rearrangement
2.3 Wulff–Dötz Reaction
2.4 Oxidative Bergman Cyclization
2.5 Diels–Alder Strategies
2.5.1 Ketene–Enol Equivalents
2.5.2 Bisketene Equivalents
3 Toward an Improved Bisketene Equivalent
4 Conclusion
Publication History
Received: 17 February 2022
Accepted after revision: 28 February 2022
Article published online:
27 June 2022
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An important exception includes the use of arynes as dienophiles. For examples, see:
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The same Diels–Alder strategy has been used for the synthesis of various ubiquinone derivatives:
Adapted from stability studies developed by Sherburn and co-workers:
For reviews, see:
For examples, see: