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A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene

Bon, David J.-Y. D; Banwell, Martin; Willis, Anthony

Description

The first total synthesis of the hirsutene-type sesquiterpenoid natural product (+)-connatusin B (2) is reported. The cis-1,2-dihydrocatechol 3, which is obtained in enantiomerically pure form via the enzymatic dihydroxylation of toluene, served as the starting material. Diels-Alder cycloaddition and oxa-di-π-methane rearrangement reactions represent key chemical steps in the reaction sequence leading to the cyclopropane ring-fused linear triquinane 14. Reductive cleavage of the three-membered...[Show more]

CollectionsANU Research Publications
Date published: 2010
Type: Journal article
URI: http://hdl.handle.net/1885/57495
Source: Tetrahedron
DOI: 10.1016/j.tet.2010.07.059

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