A Direct Asymmetric Synthesis of Juglomycin A

Juglomycin A has been synthesized in four steps from 5-methoxy-1-naphthol

Synthesis of 1,4-Phenanthrenequinones via Stannic Chloride-Induced Cyclizations

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.

Hydrogen atom abstraction reactions in organic synthesis. A formal total synthesis of racemic podophyllotoxin

The key step in a synthesis of 1 was a tandem photoenolization/Diels-Alder reaction to produce 11. Hydrolysis of the acetal and ester followed by oxidation afforded 15, an advanced intermediate in the Meyers synthesis of 1