Health & Environmental Research Online (HERO)


Print Feedback Export to File
6837559 
Journal Article 
Synthesis of the Tetracyclic Cores of the Integrastatins, Epicoccolide A and Epicocconigrone A 
Jeong, JY; Sperry, J; Brimble, MA 
2019 
Yes 
Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 
v. 84 
no. 18 
11935-11944 
English 
31416308 
WOS:000487576900053 
The integrastatins, epicoccolide A and epicoccongirone A, are natural products containing a unique [6.6.6.6]-tetracyclic core framework that exhibit a broad spectrum of biological activities. A synthesis of the common core of epicoccolide A and epicocconigrone A has been achieved using an umpolung alkylation–lactonization to assemble an isochromanone from which the bridged 1,3-dioxane was readily assembled. A different strategy was required to access the core on the integrastatins; an initial aryllithium addition to an aldehyde, followed by oxidation and treatment of the masked dihydroxyketone with acid gave the desired core structure. 
aldehydes; bioactive properties; chemical structure; dioxane; oxidation