A chemoenzymatic synthesis of the linear triquinane (−)-hirsutene and identification of possible precursors to the naturally occurring (+)-enantiomer |
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Authors: | Martin G Banwell Alison J Edwards Gwion J Harfoot Katrina A Jolliffe |
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Institution: | Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia |
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Abstract: | 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 accessing (+)-hirsutene from the original starting material. |
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Keywords: | Chemoenzymatic Hirsutene Sesquiterpene Triquinane Oxa-di-π-methane Enantiodivergence Cycloaddition cis-1 2-Dihydrocatechol |
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