A Step‐Economic Synthesis of (S)‐(−)‐Juglomycin C and (S)‐(−)‐NHAB by Dötz Benzannulation and Convergent Deprotections

Abstract A step‐economic stereoselective synthesis of ( S )‐(−)‐juglomycin C and ( S )‐(−)‐NHAB is described. The synthesis features Dötz benzannulation reaction to readily assemble the desired naphthalene structure. The key alkyne fragment was synthesized via a Jacobsen hydrolytic kinetic resolution of racemic epoxide followed by regioselective ring opening. The convergent quinone formation and TBS group removal with ceric ammonium nitrate (CAN) and also AlCl 3 ‐mediated demethylation and tert ‐butyl group removal in a convergent deprotection are notable features in the synthesis.