Toward a total synthesis of Englerin A

Goebel, Erik S.
2014-12
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Toward a total synthesis of Englerin A

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2014-12

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Englerin A is a guiane sesquiterpenoid isolated from the spurred potato-bush Phyllanthus engleri that has shown potent and selective activity against renal cancer cell lines. Our approach to the synthesis of englerin A features a Diels-Alder reaction between an axially chiral allene and a 3-siloxyfuran. We have found the oxabicyclo[2.2.1]heptane framework to be a sterically formidable structure and have discovered a novel decomposition pathway of acetyl-oxabicyclo[2.2.1]heptanes to 3(2H)-furanones.

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University of Minnesota Ph.D. dissertation. December 2014. Major: Chemistry. Advisor: Andrew M. Harned. 1 computer file (PDF); xi, 122 pages.

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Goebel, Erik S.. (2014). Toward a total synthesis of Englerin A. Retrieved from the University Digital Conservancy, https://hdl.handle.net/11299/172141.

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