Synthetic approaches to the Manumycin A, B and C antibiotics: The first total synthesis of (+)-Manumycin A

✍ Scribed by Lilian Alcaraz; Gregor Macdonald; Jacques Ragot; Norman J. Lewis; Richard J.K. Taylor

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 741 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00879-5

✦ Synopsis

The first total synthesis of Manamycin A, as its (+)-enantiomer, is reported. The synthetic route feattwes an asymmetric epoxidation (based on Wynberg's chirai phase transfer methodology) for the preparation of the key epoxyquinol nucleus, and a further demonstration of the utility of the Stifle reaction for the construction of the Manumycin lower side chain. This synthesis of Manumycin A corrects the original stereochemieal assignment and coufu'ms the syn.hydroxy epoxide arrangement. The first syntheses of the qninones obtained by the oxidative degradation of Mannmycins A-C are also described.