130595-24-3Relevant academic research and scientific papers
Isolation, synthesis and bioactivity studies of phomactin terpenoids
Kuroda, Yusuke,Nicacio, Karen J.,da Silva-Jr, Ildefonso Alves,Leger, Paul R.,Chang, Stanley,Gubiani, Juliana R.,Deflon, Victor M.,Nagashima, Nozomu,Rode, Alexander,Blackford, Katherine,Ferreira, Antonio G.,Sette, Lara D.,Williams, David E.,Andersen, Raymond J.,Jancar, Sonia,Berlinck, Roberto G. S.,Sarpong, Richmond
, p. 938 - 945 (2018)
Studies of secondary metabolites (natural products) that cover their isolation, chemical synthesis and bioactivity investigation present myriad opportunities for discovery. For example, the isolation of novel secondary metabolites can inspire advances in chemical synthesis strategies to achieve their practical preparation for biological evaluation. In the process, chemical synthesis can also provide unambiguous structural characterization of the natural products. Although the isolation, chemical synthesis and bioactivity studies of natural products are mutually beneficial, they are often conducted independently. Here, we demonstrate the benefits of a collaborative study of the phomactins, diterpenoid fungal metabolites that serve as antagonists of the platelet activating factor receptor. Our isolation of novel phomactins has spurred the development of a bioinspired, unified approach that achieves the total syntheses of six congeners. We also demonstrate in vitro the beneficial effects of several phomactins in suppressing the rate of repopulation of tumour cells following gamma radiation therapy.
C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins
Chang, Stanley,Jurczyk, Justin,Kuroda, Yusuke,Leger, Paul R.,Sarpong, Richmond
, p. 15536 - 15547 (2020)
The rearrangement of carbon-carbon (C-C) single bonds in readily available carbocyclic scaffolds can yield uniquely substituted carbocycles that would be challenging to construct otherwise. This is a powerful and often non-intuitive approach for complex m
Total synthesis of (+)-phomactin A using a B-alkyl Suzuki macrocyclization
Mohr, Peter J.,Halcomb, Randall L.
, p. 1712 - 1713 (2007/10/03)
A total synthesis of (+)-phomactin A is described using a B-alkyl Suzuki macrocyclization to incorporate the isolated trisubstituted olefin. This macrocyclization was accomplished with the sensitive hydrated furan ring in place. (R)-(+)-pulegone was used
