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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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  • Sharma Mukesh K., Banwell Martin G., Willis Anthony C.: Generation of (+)-Prezizanol, (+)-Prezizaene, and the ent -β-Isopipitzol Framework via Cationic Rearrangement of Khusiol and Related Compounds. Asian Journal of Organic Chemistry 2014, n/a. <http://dx.doi.org/10.1002/ajoc.201400019>
  • Vo Yen, Banwell Martin G., Willis Anthony C.: Chemoenzymatic Routes to Polyoxygenated Cyclooctenones Related to the Eastern Hemisphere of the Macrolactam Tripartilactam. Chem. Asian J. 2014, 9, 67. <http://dx.doi.org/10.1002/asia.201301233>
  • Lan Ping, Banwell Martin G., Willis Anthony C.: Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties. J. Org. Chem. 2014, 79, 2829. <http://dx.doi.org/10.1021/jo500210k>
  • Lan Ping, Banwell Martin G., Ward Jas S., Willis Anthony C.: Chemoenzymatic Total Synthesis and Reassignment of the Absolute Configuration of Ribisin C. Org. Lett. 2014, 16, 228. <http://dx.doi.org/10.1021/ol403220t>
  • Froese Jordan, Endoma-Arias Mary Ann A., Hudlicky Tomas: Processing of o-Halobenzoates by Toluene Dioxygenase. The Role of the Alkoxy Functionality in the Regioselectivity of the Enzymatic Dihydroxylation Reaction. Org. Process Res. Dev. 2014, 140210093708009. <http://dx.doi.org/10.1021/op400343c>
  • Lewis Simon E.: Applications of biocatalytic arene ipso,ortho cis-dihydroxylation in synthesis. Chem. Commun. 2014, 50, 2821. <http://dx.doi.org/10.1039/c3cc49694e>
  • Griffen Julia A., Kenwright Sarah J., Abou-Shehada Sarah, Wharry Scott, Moody Thomas S., Lewis Simon E.: Benzoate dioxygenase from Ralstonia eutropha B9 – unusual regiochemistry of dihydroxylation permits rapid access to novel chirons. Org. Chem. Front. 2014, 1, 79. <http://dx.doi.org/10.1039/c3qo00057e>
  • Vila María Agustina, Brovetto Margarita, Gamenara Daniela, Bracco Paula, Zinola Guillermo, Seoane Gustavo, Rodríguez Sonia, Carrera Ignacio: Production of cis-1,2-dihydrocatechols of high synthetic value by whole-cell fermentation using Escherichia coli JM109 (pDTG601): A detailed study. Journal of Molecular Catalysis B: Enzymatic 2013, 96, 14. <http://dx.doi.org/10.1016/j.molcatb.2013.06.003>
  • Trant John F., Froese Jordan, Hudlicky Tomas: Enzymatic oxidation of para-substituted arenes: access to new non-racemic chiral metabolites for synthesis. Tetrahedron: Asymmetry 2013, 24, 184. <http://dx.doi.org/10.1016/j.tetasy.2013.01.002>
  • Reekie Tristan A., Banwell Martin G., Willis Anthony C.: Intramolecular Cycloaddition Reactions of cis-1,2-Dihydrocatechol Derivatives Incorporating C3-Tethered Diazoketones, Nitrile Oxides, and Azides: Stereocontrolled Routes to Enantiomerically Pure Spiro[5.5]undecanes and Related Systems. J. Org. Chem. 2013, 78, 7100. <http://dx.doi.org/10.1021/jo400952u>
  • Ramos Juan Carlos, Brovetto Margarita, Seoane Gustavo A.: Chemoenzymatic Synthesis of trans-Tetrahydrofuran Cores of Annonaceous Acetogenins from Bromobenzene. Org. Lett. 2013, 15, 1982. <http://dx.doi.org/10.1021/ol400650v>
  • Ali Khan Monika, Mahon Mary F., Lowe John P., Stewart Alan J. W., Lewis Simon E.: Valuable New Cyclohexadiene Building Blocks from Cationic η5 -Iron-Carbonyl Complexes Derived from a Microbial Arene Oxidation Product. Chem. Eur. J. 2012, 18, 13480. <http://dx.doi.org/10.1002/chem.201202411>
  • 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>
  • Dietinger Christine E., Banwell Martin G., Garson Mary J., Willis Anthony C.: Chemoenzymatic and enantioselective assembly of the (1α,3aβ,6α,7aβ)-octahydro-1,6-methano-1H-indene framework associated with 2-isocyanoallopupukeanane: validation of a new synthetic strategy and the identification of enantiomeric switching regimes. Tetrahedron 2010, 66, 5250. <http://dx.doi.org/10.1016/j.tet.2010.04.056>
  • Bon David J.-Y.D., Banwell Martin G., Willis Anthony C.: A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene. Tetrahedron 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, Banwell Martin G., Willis Anthony C.: A chemoenzymatic total synthesis of ent-narciclasine. Tetrahedron 2008, 64, 4817. <http://dx.doi.org/10.1016/j.tet.2008.01.113>
  • Kokas Okanya J., Banwell Martin G., Willis Anthony C.: Chemoenzymatic approaches to the montanine alkaloids: a total synthesis of (+)-nangustine. Tetrahedron 2008, 64, 6444. <http://dx.doi.org/10.1016/j.tet.2008.04.070>
  • 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, Edwards Alison J, Harfoot Gwion J, Jolliffe Katrina A: A chemoenzymatic synthesis of the linear triquinane (−)-hirsutene and identification of possible precursors to the naturally occurring (+)-enantiomer. Tetrahedron 2004, 60, 535. <http://dx.doi.org/10.1016/j.tet.2003.10.122>
  • 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>