Angucycline is a subclass of natural antibiotics, containing a characteristic tetracyclic ring structure, and featuring a wide range of biological functions, including antitumor, antiviral and antifungal properties. This extraordinarily therapeutic character has interested many chemists to develop efficient methodologies for synthesizing the tetracyclic ring system of angucycline. Construction of the BC ring configuration appears as a synthetic challenge. Successful installation of hydroxyl groups at the AB junction would pave the way for efficient syntheses. As a continuation of the previous work done on this system, our synthetic methodology focuses on the coupling of a suitably substituted Phthalide and an activated Alkyne through a tandem Michael addition/Dieckmann cyclization. The synthesis of the required phthalide and alkyne components is discussed, as well as our efforts towards the coupling components.
Allaoa, Abdullah; Nicolas, Tony E.; and Wu, Xiaolan, "Synthesis of a Model of the BC Ring System of Oxygenated Angucyclines" (2017). CUNY Academic Works.