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Pure Appl. Chem., 2003, Vol. 75, No. 2-3, pp. 223-229

http://dx.doi.org/10.1351/pac200375020223

Chemoenzymatic methods for the enantioselective preparation of sesquiterpenoid natural products from aromatic precursors

M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart and M. Vögtle

Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia

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  • Bon David J.-Y. D., Banwell Martin G., Cade Ian A., Willis Anthony C.: The total synthesis of (−)-connatusin A, a hirsutane-type sesquiterpene isolated from the fungus Lentinus connatus BCC8996. Tetrahed 2011, 67, 8348. <http://dx.doi.org/10.1016/j.tet.2011.08.057>
  • Ma Xinghua, Jury Jasmine C., Banwell Martin G.: Synthesis and reactivity of a putative biogenetic precursor to tricholomenyns B, C, D and E. Tetrahetron Lett 2011, 52, 2192. <http://dx.doi.org/10.1016/j.tetlet.2010.11.139>
  • Schwartz Brett D., Banwell Martin G., Cade Ian A.: A chemoenzymatic total synthesis of the Amaryllidaceae alkaloid narseronine. Tetrahetron Lett 2011, 52, 4526. <http://dx.doi.org/10.1016/j.tetlet.2011.06.050>
  • Schwartz Brett D., White Lorenzo V., Banwell Martin G., Willis Anthony C.: Structure of the Lycorinine Alkaloid Nobilisitine A. J Org Chern 2011, 76, 8560. <http://dx.doi.org/10.1021/jo2016899>
  • Banwell Martin G., Lehmann Anna L., Menon Rajeev S., Willis Anthony C.: New methods for the synthesis of certain alkaloids and terpenoids. Pure and App Chemis 2011, 1. <http://dx.doi.org/10.1351/PAC-CON-10-10-21>
  • Banwell Martin G., Gao Nadia Yuqian, Ma Xinghua, Petit Laurent, White Lorenzo V., Schwartz Brett D., Willis Anthony C., Cade Ian A.: gem-Dibromocyclopropanes and enzymatically derived cis-1,2-dihydrocatechols as building blocks in alkaloid synthesis. PureAppl Chem 2011, 1. <http://dx.doi.org/10.1351/PAC-CON-11-07-05>
  • Bon David J.-Y.D., Banwell Martin G., Willis Anthony C.: A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene. Tetrahed 2010, 66, 7807. <http://dx.doi.org/10.1016/j.tet.2010.07.059>
  • Lin Andrew, Willis Anthony C., Banwell Martin G.: A chemoenzymatic and enantioselective total synthesis of the resorcylic acid lactone L-783,290, the trans-isomer of L-783,277. Tetrahetron Lett 2010, 51, 1044. <http://dx.doi.org/10.1016/j.tetlet.2009.12.067>
  • Austin Kerrie A. B., Elsworth Jon D., Banwell Martin G., Willis Anthony C.: Chemoenzymatic and enantiodivergent routes to 1,2-ring-fused bicyclo[2.2.2]octane and related tricyclic frameworks. Org Biomol Chem 2010, 8, 751. <http://dx.doi.org/10.1039/b921600f>
  • Matveenko Maria, Banwell Martin G., Joffe Max, Wan Soosan, Fantino Emmanuelle: Biological Evaluation of ent-Narciclasine, ent-Lycoricidine, and Certain Enantiomerically-Related Congeners. C&B 2009, 6, 685. <http://dx.doi.org/10.1002/cbdv.200800319>
  • Bellomo Ana, Camarano Soledad, Rossini Carmen, Gonzalez David: Enantiospecific synthesis and insect feeding activity of sulfur-containing cyclitols. Carbohydrates Research 2009, 344, 44. <http://dx.doi.org/10.1016/j.carres.2008.09.026>
  • Findlay Alison D., Gebert Antje, Cade Ian A., Banwell Martin G.: The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin. Aust J Chem 2009, 62, 1173. <http://dx.doi.org/10.1071/CH09283>
  • Shie Jiun‐Jie, Fang Jim‐Min, Wong Chi‐Huey: A Concise and Flexible Synthesis of the Potent Anti‐Influenza Agents Tamiflu and Tamiphosphor. Angew Chem 2008, 120, 5872. <http://dx.doi.org/10.1002/ange.200801959>
  • Shie Jiun‐Jie, Fang Jim‐Min, Wong Chi‐Huey: A Concise and Flexible Synthesis of the Potent Anti‐Influenza Agents Tamiflu and Tamiphosphor. Angew Chem Int Ed 2008, 47, 5788. <http://dx.doi.org/10.1002/anie.200801959>
  • Bellomo Ana, Gonzalez David, Stefani Hèlio A.: Synthesis of unnatural cyclitols via a combined enzymatic-palladium catalysis approach. J Organomet Chem 2008, 693, 1136. <http://dx.doi.org/10.1016/j.jorganchem.2008.01.006>
  • Matveenko Maria, Willis Anthony C., Banwell Martin G.: A chemoenzymatic synthesis of the anti-influenza agent Tamiflu®. Tetrahetron Lett 2008, 49, 7018. <http://dx.doi.org/10.1016/j.tetlet.2008.09.130>
  • Banwell Martin G., Edwards Alison J., Lupton David W., Whited Gregg: Whole-Cell Biotransformation of m-Ethyltoluene into 1S,6R-5-Ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic Acid as an Approach to the C-Ring of the Binary Indole?Indoline Alkaloid Vinblastine . Aust J Chem 2005, 58, 14. <http://dx.doi.org/10.1071/CH04185>
  • Banwell Martin G., Harfoot Gwion J.: A Chemoenzymatic and Enantioselective Route to the Tricyclic Frameworks Associated with the Protoilludane and Marasmane Classes of Sesquiterpene. Aust J Chem 2004, 57, 895. <http://dx.doi.org/10.1071/CH04131>
  • Banwell Martin G., Edwards Alison J., Harfoot Gwion J., Jolliffe Katrina A., McLeod Malcolm D., McRae Kenneth J., Stewart Scott G., Vogtle Markus: Chemoenzymatic Methods for the Enantioselective Preparation of Sesquiterpenoid Natural Products from Aromatic Precursors. ChemInform 2003, 34. <http://dx.doi.org/10.1002/chin.200342269>