Synthesis of 1,4-Phenanthrenequinones via Stannic Chloride-Induced Cyclizations
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Abstract
Substituted 1,4-phenanthrenequinones such as 1 are useful building blocks for the preparation of novel materials. Katz and others have shown that compounds such as 1 can be transformed into helicenes by DielsAlder reactions.1 Certain 1,4-phenanthrenequinones also have potential as synthetic intermediates for natural products synthesis. Additionally, some naturally occurring 1,4-phenanthrenequinones such as cypripedium (2) are biologically active.2 Kraus and Carpenter have determined that some 1,4-phenanthrenequinones exhibit inhibitory activity in vitro against the equine infectious anemia virus.3
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Reprinted (adapted) with permission from The Journal of Organic Chemistry, 64(5); 1720-1722. Doi: 10.1021/jo981352f. Copyright 1999 American Chemical Society.