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|Title:||Bisketene equivalents as diels-alder dienes|
|Citation:||Journal of the American Chemical Society, 2020; 142(31):13328-13333|
|Isuru Dissanayake, Jacob D. Hart, Emma C. Becroft, Christopher J. Sumby and Christopher G. 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.|
|Keywords:||Redox reactions; organic synthesis; reaction products; cyclization; chemical synthesis|
|Rights:||© 2020 American Chemical Society|
|Appears in Collections:||Chemistry and Physics publications|
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