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Rapid construction of the ABD tricyclic skeleton in meliacarpinin B from carvone enabled by an INOC strategy

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A highly diastereoselective synthesis of the ABD skeleton of meliacarpinin B is presented. The construction of the key trans-decalin unit features an intramolecular nitrile oxide-alkene cycloaddtion (INOC) reaction on a… Click to show full abstract

A highly diastereoselective synthesis of the ABD skeleton of meliacarpinin B is presented. The construction of the key trans-decalin unit features an intramolecular nitrile oxide-alkene cycloaddtion (INOC) reaction on a readily available carvone derivative. This strategy enabled prepration of the tricyclic core bearing 6 contiguous stereogenic centres in 14 straightforward linear steps from R-carvone.

Keywords: construction; skeleton meliacarpinin; skeleton; strategy; carvone

Journal Title: Organic chemistry frontiers
Year Published: 2020

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