Department of Pharmaceutical Sciences, University of Connecticut, Storrs, CT 06269, USA.
Molecules. 2013 Feb 21;18(2):2438-48. doi: 10.3390/molecules18022438.
Phelligridin G is an unusual natural product that contains an embedded spiro-fused furanone core. We have investigated two furan-based synthetic approaches towards the spirocyclic core structure of this natural product from readily available 2-phenylfurans. Although initial studies involving an oxidative cyclization were unsuccessful, we were ultimately able to access this key system through a sequential intermolecular furan Diels-Alder reaction followed by a metathesis-based reorganization. A related approach led to an expanded C ring to form spiro-fused pyran spirocycles.
Phelligridin G 是一种不寻常的天然产物，其中包含一个嵌入式的螺环稠合呋喃酮核心。我们研究了两种基于呋喃的合成方法，从易得的 2-苯基呋喃出发，来构建这个天然产物的螺环核心结构。虽然最初涉及氧化环化的研究没有成功，但我们最终能够通过连续的分子间呋喃 Diels-Alder 反应和随后的基于复分解的重排来获得这个关键体系。一种相关的方法导致了扩大的 C 环，形成了螺环稠合的吡喃螺环。
