77220-16-7Relevant academic research and scientific papers
CHEMISTRY OF 2,5-BIS(TRIMETHYLSILOXY)FURANS. I: PREPARATION AND DIELS-ALDER REACTIONS
Brownbridge, Peter,Chan, Tak-Hang
, p. 3423 - 3426 (1980)
A number of substituted 2,5-bis(trimethylsiloxy)furans were prepared from the corresponding succinic anhydrides, and were found to be reactive dienes from the Diels-Alder reaction with electron-withdrawing dienophiles, giving p-quinones and hydroquinones.
Bisketene Equivalents as Diels-Alder Dienes
Dissanayake, Isuru,Hart, Jacob D.,Becroft, Emma C.,Sumby, Christopher J.,Newton, Christopher G.
supporting information, p. 13328 - 13333 (2020/09/03)
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.
