Joo Young Jeong, J. Sperry, M. Brimble
Aug 16, 2019
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0
Influential Citations
7
Citations
Journal
The Journal of organic chemistry
Abstract
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-lactonisation 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.