Issue 43, 2019

A general synthesis of dendralenes


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

Supplementary files

Article information

Article type
Edge Article
09 Aug 2019
11 Sep 2019
First published
12 Sep 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2019,10, 9969-9973

A general synthesis of dendralenes

J. George, J. S. Ward and M. S. Sherburn, Chem. Sci., 2019, 10, 9969 DOI: 10.1039/C9SC03976G

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