Synthesis of Protected 4‐Deoxyaklanonic Acid via Naphthalene‐substituted Oligoketides

Ketide side chains (C 4 ) were attached to the naphthoquinone 3 by reaction with the dienes 4 or 14 followed by Baker‐Venkataraman rearrangement of esters 8 and 17 to attach the second protected β‐diketo side chain. Linear anellations of the corresponding naphthoquinone precursors 9 and 17 to the 4‐deoxyaklanonic acids 10 and 18a , respectively, were effected in a base‐catalyzed cascade of reactions (e.g. only three operations from 3 to 18a ).