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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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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.

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

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Article information


Submitted
11 May 2020
Accepted
10 Jun 2020
First published
17 Jun 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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

C. Dong, T. Qiao, Y. Xie, X. Zhang, J. Ao and G. Liang, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00576B

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