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Masked Bisketenes as Diels–Alder Dienes

preprint
submitted on 11.06.2020, 06:27 and posted on 12.06.2020, 11:03 by Isuru Dissanayake, Jacob Hart, Emma Becroft, Christopher Sumby, Christopher Newton

2,5-Bis(tert-butyldimethylsilyloxy)furans are established as masked vicinal bisketenes for application as dienes in the Diels–Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels–Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.

Funding

Molecular complexity through multi-bond forming reactions

Australian Research Council

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History

Email Address of Submitting Author

chris.newton@uga.edu

Institution

University of Georgia

Country

United States

ORCID For Submitting Author

0000-0002-8962-5917

Declaration of Conflict of Interest

None

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in Journal of the American Chemical Society

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