Abstract
An approach for the synthesis of lignans related to the podophyllotoxin family is
reported. The key reaction is a highly diastereoselective iodoacetal cyclization
under iodine atom transfer conditions followed by a homolytic aromatic substitution.
The second aromatic ring is introduced at a later stage via addition of aryllithium
to an aryl ketone. A novel and very mild method for the deoxygenation of the intermediate
tertiary benzylic alcohols is described.
Key words
radicals - iodoacetals - lignans - podophyllotoxin - deoxygenation - benzylic alcohols
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