Bisketene Equivalents as Diels-Alder Dienes

Journal of the American Chemical Society
Isuru DissanayakeChristopher Newton

Abstract

2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents 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.

References

May 25, 2002·Journal of Natural Products·Leng Chee ChangCarole A Bewley
May 19, 2006·Organic Letters·Christopher C LindseyThomas R R Pettus
Nov 9, 2006·Beilstein Journal of Organic Chemistry·E J Behrman
Apr 21, 2007·Chemical Reviews·Dipakranjan Mal, Pallab Pahari
Sep 1, 2007·Journal of the American Chemical Society·Barry M TrostDaniel B Horne
Jan 22, 2010·Archives of Pharmacal Research·Santosh K GurungHaeil Park
Mar 3, 2012·Natural Product Reports·Suthananda N Sunassee, Michael T Davies-Coleman
Aug 16, 2013·The Journal of Organic Chemistry·Feyza KarasuNicholas J Turro
Aug 29, 2013·The Journal of Antibiotics·Yoichi HayakawaMasumi Izawa
Mar 4, 2014·The Journal of Organic Chemistry·Thomas FallonMichael S Sherburn
Oct 11, 2014·Journal of the American Chemical Society·Jose M MedinaK N Houk
Nov 22, 2019·Journal of the American Chemical Society·Kelsey L HorvathMichael S Sherburn

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Citations

Jul 8, 2021·Organic & Biomolecular Chemistry·Christopher D GabbuttDimitrios Zonidis
Oct 7, 2020·Organic Letters·Adam J ZaharaSidney M Wilkerson-Hill

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