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A general synthesis of dendralenes

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Abstract

The first general synthetic approach to substituted [3]- and higher dendralenes is reported. Fifty-one mono- through to penta-substituted dendralenes carrying alkyl-, cycloalkyl-, alkenyl-, alkynyl-, aryl- and heteroaryl-substitutents are accessed, and the first (E)/(Z)-stereoselective syntheses of dendralenes are reported (twenty-eight examples). The approach involves twofold Pd(0)-catalyzed Negishi couplings of 1,1-dibromoalkenes with alkenylzinc reagents, and exploits both substrate- and catalyst-controlled aspects of chemo-, regio- and stereoselectivity in the two C(sp2)–C(sp2) bond forming steps. The value of the new hydrocarbons in rapid structural complexity generation is demonstrated through their deployment in unprecedented diene- and triene-transmissive pericyclic reaction sequences.

Graphical abstract: A general synthesis of dendralenes

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Publication details

The article was received on 09 Aug 2019, accepted on 11 Sep 2019 and first published on 12 Sep 2019


Article type: Edge Article
DOI: 10.1039/C9SC03976G
Chem. Sci., 2019, Advance Article
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    A general synthesis of dendralenes

    J. George, J. S. Ward and M. S. Sherburn, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03976G

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