Enantiospecific Total Synthesis of (−)-Bengamide E

Total synthesis of the polyhydroxy caprolactam amide natural product, bengamide E, is accomplished starting from tartaric acid. Key reactions in the synthesis include desymmetrization of the bis(dimethylamide) unit of tartaric acid, Zn(BH4)2‐mediated anti‐selective reduction, and a Horner–Wadsworth–Emmons olefination. Concise approach with control: A total synthesis of the polyhydroxy caprolactam amide natural product bengamide E from tartaric acid has been described. The key reactions include the elaboration of the bis(dimethylamide) unit of tartaric acid and involves 1,3‐dithiane addition and a Horner–Wadsworth–Emmons olefination.