A four-step route to synthetic equivalents of ortho-xylylenes: Dotz benzannulation, desilylation, bromo-dehydroxylation, and sultine formation. A concise approach to oxygenated linearly fused polycyclic aromatics

A new route has been reported for the synthesis of densely oxygenated polycyclic aromatic compounds via cycloaddition approach. This strategy involves the Dotz benzannulation and Diels-Alder reaction as key steps. Naphthalene synthons required here were generated by Dotz benzannulation between aryl chromium carbene complexes and symmetrical internal alkyne. (C) 2016 Elsevier Ltd. All rights reserved.