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A Chemoenzymatic Synthesis of the Linear Triquinane (?)-Hirsutene and Identification of Possible Precursors to the Naturally Occurring (+)-Enantiomer

Banwell, Martin; Edwards, Alison; Harfoot, Gwion; Jolliffe, Katrina

Description

An enantiomerically pure cis-1,2-dihydrocatechol, which is readily obtained via a toluene dioxygenase-mediated dihydroxylation of toluene in a whole-cell biotransformation process, has been converted over 17 steps into the linear triquinane (-)-hirsutene. Since the enantiomer of the starting material is also available this work constitutes a formal total synthesis of the naturally occurring (+)-form of hirsutene. Furthermore, minor modifications of the route used here offer the possibility of...[Show more]

CollectionsANU Research Publications
Date published: 2004
Type: Journal article
URI: http://hdl.handle.net/1885/78361
Source: Tetrahedron
DOI: 10.1016/j.tet.2003.10.122

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