A strategy based on bidirectional Dötz benzannulation and the oxa-Pictet-Spengler reaction toward the synthesis of actinorhodin and γ-actinorhodin has been explored. This work has resulted in the synthesis of deoxyactinorhodin and deoxy-γ-actinorhodin. The latter is a regioisomer of crisamicin A (which has 10,10'-dihydroxy groups).