Bioinspired Total Synthesis of Bussealin E.

Org Lett

Department of Chemistry , University of Cambridge, Lensfield Road , Cambridge CB2 1EW , U.K.

Published: March 2018

AI Article Synopsis

  • The first total synthesis of bussealin E, a compound with a unique structure, has been successfully achieved.
  • The synthesis strategy was inspired by a proposed natural biosynthesis and involved creating a tetracyclic ring system through oxidative phenolic coupling.
  • A crucial step in this process was the sp-sp Hiyama coupling, which combined a vinyldisiloxane with a benzylic bromide to form the necessary diphenylpropane derivative.

Article Abstract

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 sp-sp Hiyama coupling between a vinyldisiloxane and a benzylic bromide.

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Source
http://dx.doi.org/10.1021/acs.orglett.8b00340DOI Listing

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