Domino retro Diels–Alder/Diels–Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones
Organic & Biomolecular Chemistry Pub Date: 2006-05-04 DOI: 10.1039/B602928K
Abstract
A novel and convenient approach, the domino retro Diels–Alder/Diels–Alder reaction sequence for highly stereo- and regioselective synthesis of various bicyclo[2.2.2]octenone and bicyclo[2.2.2]octadienone derivatives is presented. Thus, the masked o-benzoquinones (MOBs) 2a–e generated by the pyrolysis of the respective dimers 3a–e participated in this novel synthetic strategy with a variety of olefinic and acetylenic dienophiles at 220 °C to provide the title compounds in good to excellent yields.
![Graphical abstract: Domino retro Diels–Alder/Diels–Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones](http://scimg.chem960.com/usr/1/B602928K.jpg)
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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