80155-95-9Relevant articles and documents
Carbene-Catalyzed Formal [5 + 5] Reaction for Coumarin Construction and Total Synthesis of Defucogilvocarcins
Huang, Xuan,Zhu, Tingshun,Huang, Zhijian,Zhang, Yuexia,Jin, Zhichao,Zanoni, Giuseppe,Chi, Yonggui Robin
, p. 6188 - 6191 (2017)
An N-heterocyclic carbene-catalyzed formal [5 + 5] reaction between enals and furanones that generates multisubstituted coumarins in a single step is reported. Five atoms in each of the substrates are involved in this catalytic process to form a benzene and a lactone ring. The power of the method is further demonstrated in metal-free total syntheses of several natural products (defucogilvocarcins M, E, and V) bearing coumarin as the key structural motif.
An inverse electron demand Diels-Alder-based total synthesis of defucogilvocarcin V and some C-8 analogues
Nandaluru, Penchal Reddy,Bodwell, Graham J.
, p. 8028 - 8037,10 (2020/10/15)
A concise total synthesis of defucogilvocarcin V is reported. The key features of the approach are the formation of the C-ring using a vinylogous Knoevenagel/transesterification reaction and construction of the D-ring by way of an inverse electron demand Diels-Alder-driven domino reaction. The resulting C-8 ester functionality provides a handle for the synthesis of defucogilvocarcin V as well as some C-8 analogues from a common late-stage intermediate.
Combined directed metalation-cross coupling strategies. Total synthesis of the aglycones of gilvocarcin V, M and E
James, Clint A.,Snieckus, Victor
, p. 8149 - 8152 (2007/10/03)
Using the versatile Directed ortho and remote Metalation protocols linked with Suzuki-Miyaura cross coupling, efficient syntheses of defucogilvocarcin V, M, and E, 2-4 have been achieved.