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Org Lett. 2013 Jan 4;15(1):14-7. doi: 10.1021/ol3028658. Epub 2012 Dec 13.

Palladium-promoted [2 + 2 + 2] cocyclization of arynes and unsymmetrical conjugated dienes: synthesis of justicidin B and retrojusticidin B.

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1
Division of Organic Chemistry, National Chemical Laboratory (CSIR), Pune 411 008, India.

Abstract

A facile synthesis of natural and unnatural arylnaphthalenes has been demonstrated via the unprecedented palladium-promoted [2 + 2 + 2] cocyclization of arynes and unsymmetrical conjugated dienes using the N-heterocyclic carbene as a ligand. The unsymmetrical dienes used herein are actually α-coupled acrylate-cinnamate combinations bearing two β-positive carbons and follow the key [2 + 2 + 2] cocyclization pathway.

PMID:
23237050
DOI:
10.1021/ol3028658
[Indexed for MEDLINE]
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