Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates

Angewandte Chemie
Johannes M WiestM Kevin Brown

Abstract

The first synthesis of hebelophyllene E is presented, along with assignment of its previously unknown relative configuration through synthesis of epi-ent-hebelophyllene E. Development of a catalytic enantioselective [2+2] cycloaddition of alkenes and allenoates provides access to the required chiral geminal dimethylcyclobutanes. Key to its success is the identification of a novel oxazaborolidine catalyst which promotes the cycloaddition in high enantioselectivities with good functional-group tolerance (9 examples, up to 97:3 e.r.). Thus, a late-stage cycloaddition using a fully functionalized alkene, followed by a diastereoselective reduction allows a concise entry to this class of natural products.

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Citations

Aug 9, 2018·Angewandte Chemie·Frederik KrammBernd Plietker
Mar 12, 2019·Natural Product Reports·Erin N HancockM Kevin Brown
Oct 28, 2019·Angewandte Chemie·Erin N HancockM Kevin Brown
Aug 19, 2020·Organic Letters·Andrea SerafinoGiovanni Maestri
Mar 10, 2020·Journal of the American Chemical Society·Renyu GuoM Kevin Brown
Nov 6, 2018·Journal of the American Chemical Society·Johannes M WahlM Kevin Brown
May 31, 2019·Journal of the American Chemical Society·Mary Elisabeth DaubTehshik P Yoon

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