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Bioinspired Total Synthesis of Bussealin E

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journal contribution
posted on 01.03.2018 by David G. Twigg, Leonardo Baldassarre, Elizabeth C. Frye, Warren R. J. D. Galloway, David R. Spring
The first total synthesis of bussealin E, a natural product with a unique cycloheptadibenzofuran scaffold, is reported. A strategy inspired by a proposed biosynthesis was employed whereby a diphenylpropane derivative underwent an oxidative phenolic coupling to forge the tetracyclic ring system. The synthesis of the diphenylpropane featured a key sp2–sp3 Hiyama coupling between a vinyldisiloxane and a benzylic bromide.