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Pure Appl. Chem., 1992, Vol. 64, No. 12, pp. 1821-1830

New methods and strategies for the stereocontrolled synthesis of polypropionate-derived natural products

I. Paterson

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  • McLaughlin Mark G., Cook Matthew J.: Highly diastereoselective hydrosilylations of allylic alcohols. Chem. Commun. 2014, 50, 3501. <>
  • Paterson Ian, Steadman neé Doughty Victoria A., McLeod Malcolm D., Trieselmann Thomas: Stereocontrolled total synthesis of (+)-concanamycin F: the strategic use of boron-mediated aldol reactions of chiral ketones. Tedrahedron 2011, 67, 10119. <>
  • Mochirian Philippe, Godin François, Katsoulis Ioannis, Fontaine Isabelle, Brazeau Jean-François, Guindon Yvan: A Bidirectional Approach to the Synthesis of Polypropionates: Synthesis of C1–C13 Fragment of Zincophorin and Related Isomers. J Org Chern 2011, 76, 7654. <>
  • PATERSON I.: ChemInform Abstract: New Methods and Strategies for the Stereocontrolled Synthesis of Polypropionate-Derived Natural Products. ChemInform 2010, 24, no. <>
  • Marcaurelle Lisa A., Comer Eamon, Dandapani Sivaraman, Duvall Jeremy R., Gerard Baudouin, Kesavan Sarathy, Lee Maurice D., Liu Haibo, Lowe Jason T., Marie Jean-Charles: An Aldol-Based Build/Couple/Pair Strategy for the Synthesis of Medium- and Large-Sized Rings: Discovery of Macrocyclic Histone Deacetylase Inhibitors. J Am Chem Soc 2010, 132, 16962. <>
  • Geary Laina M., Hultin Philip G.: The state of the art in asymmetric induction: the aldol reaction as a case study. Tet Asymm 2009, 20, 131. <>
  • Ogini Francis O., Elder Philip J. W., Britten James F., Vargas-Baca Ignacio: An investigation of (C5H5)Fe(C5H4–C(OBF3)–CH3)1,2. Can J Chem 2009, 87, 1055. <>
  • Bock Martin, Dehn Richard, Kirschning Andreas: Totalsynthese von Thuggacin B. Angew Chem 2008, 120, 9274. <>
  • Bock Martin, Dehn Richard, Kirschning Andreas: Total Synthesis of Thuggacin B. Angew Chem Int Ed 2008, 47, 9134. <>
  • Rauniyar Vivek, Hall Dennis G.: Catalytic Enantioselective and Catalyst-Controlled Diastereofacial-Selective Additions of Allyl- and Crotylboronates to Aldehydes Using Chiral Brønsted Acids. Angew Chem 2006, 118, 2486. <>
  • Rauniyar Vivek, Hall Dennis G.: Catalytic Enantioselective and Catalyst-Controlled Diastereofacial-Selective Additions of Allyl- and Crotylboronates to Aldehydes Using Chiral Brønsted Acids. Angew Chem Int Ed 2006, 45, 2426. <>
  • Paterson Ian, Coster Mark J., Chen David Y.-K., Oballa Renata M., Wallace Debra J., Norcross Roger D.: The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the AB-spiroacetal segment. Org Biomol Chem 2005, 3, 2399. <>
  • Paterson Ian, Coster Mark J., Chen David Y.-K., Gibson Karl R., Wallace Debra J.: The stereocontrolled total synthesis of altohyrtin A/spongistatin 1: the CD-spiroacetal segment. Org Biomol Chem 2005, 3, 2410. <>
  • Kabalka G.W, Wu Zhongzhi, Ju Yuhong: The use of organoboron chlorides and bromides in organic synthesis. J Organomet Chem 2003, 680, 12. <>
  • Arbelo David O., Castro-Rosario Leslie, Prieto José A.: Efficient Hydroxyl Inversion in Propionates via Cesium Carboxylates. Synth Common 2003, 33, 3211. <>
  • Panda Manoranjan, Kozlowski Marisa C: Computer-aided design of chiral ligands. Mol Graph Model 2002, 20, 399. <>
  • Sampson Rebecca A., Perkins Michael V.: Total Synthesis of (−)-(6S,7S,8S,9R,10S,2‘S)-Membrenone-A and (−)-(6S,7S,8S,9R,10S)- Membrenone-B and Structural Assignment of Membrenone-C. Org Lett 2002, 4, 1655. <>
  • Perkins Michael V., Sampson Rebecca A.: Stereoselective Synthesis of Dihydropyrone-Containing Marine Natural Products. Total Synthesis and Structural Elucidation of (−)-Membrenone-C. Org Lett 2001, 3, 123. <>
  • Evarts J.B., Fuchs P.L.: Synthesis of a family of epoxyvinyltriflate stereotetrads from 4-hydroxycyclohex-2-en-1-one. Tetrahetron Lett 1999, 40, 2703. <>
  • Zhong Guofu, Shabat Doron, List Benjamin, Anderson James, Sinha Subhash C., Lerner Richard A., Barbas Carlos F.: Katalytische enantioselektive Retro-Aldolreaktion: kinetische Racematspaltung von β-Hydroxyketonen durch Aldolase-Antikörper. Angew Chem 1998, 110, 2609. <<2609::AID-ANGE2609>3.0.CO;2-E>
  • Gennari Cesare, Ceccarelli Simona, Piarulli Umberto, Aboutayab Karim, Donghi Monica, Paterson Ian: Stereocontrolled synthesis of polyketide libraries: Boron-mediated aldol reactions with aldehydes on solid support. Tetrahedron 1998, 54, 14999. <>
  • Paterson Ian, Yeung Kap-Sun, Watson Christine, Ward Richard A., Wallace Paul A.: The total synthesis of scytophycin C. Part 1: stereocontrolled synthesis of the C1C32 protected seco acid. Tetrahedron 1998, 54, 11935. <>
  • Perkins Michael V., Sampson Rebecca A.: Stereoselective synthesis of an isomer of Membrenone-C via an aldol based two directional chain extension. Tetrahetron Lett 1998, 39, 8367. <>
  • Gennari Cesare, Moresca Daniela, Vulpetti Anna, Pain Gilles: Reagent control in the aldol addition reaction of chiral boron enolates with chiral aldehydes. Total synthesis of (3S,4S)-Statine. Tetrahedron 1997, 53, 5593. <>
  • Gennari Cesare, Vulpetti Anna, Pain Gilles: Highly enantio- and diastereoselective boron aldol reactions of α-heterosubstituted thioacetates with aldehydes and silyl imines. Tetrahedron 1997, 53, 5909. <>
  • Bernardi Anna, Gennari Cesare, Raimondi Laura, Villa Maria B.: Computational studies on the aldol-type addition of boron enolates to imines: An ab-initio approach. Tetrahedron 1997, 53, 7705. <>
  • Paterson Ian, Man Jocelyn: Studies in macrolide synthesis: A novel cyclodimerisation approach to the synthesis of elaiophylin using a double Stille cross-coupling reaction. Tetrahetron Lett 1997, 38, 695. <>
  • Fehr Charles: Enantioselektive Protonierung von Enolaten und Enolen. Angew Chem 1996, 108, 2726. <>
  • Ancerewicz Jacek, Vogel Pierre: A New Approach to the Synthesis of Long-Chain Polypropionates Based on theDiels-Alder Monoadditions of 2,2′-Ethylidenebis[3,5-dimethylfuran]. HCA 1996, 79, 1393. <>
  • Paterson Ian, Perkins Michael V.: Total Synthesis of (−)-Denticulatins A and B Using Efficient Methods of Acyclic Stereocontrol. Tetrahedron 1996, 52, 1811. <>
  • Ramachandran P.Veeraraghavan, Xu Wei-chu, Brown Herbert C.: Contrasting steric effects of the ketones and aldehydes in the reactions of the diisopinocampheyl enolborinates of methyl ketones with aldehydes. Tetrahetron Lett 1996, 37, 4911. <>
  • Paterson Ian, Nowak Thorsten: Anti Aldol reactions of α-alkoxymethyl ketones: Application to the total synthesis of (+)-restricticin. Tetrahetron Lett 1996, 37, 8243. <>
  • Paterson Ian, Oballa Renata M., Norcross Roger D.: Studies in marine macrolide synthesis: Stereocontrolled synthesis of the AB-spiroacetal subunit of spongistatin 1 (altohyrtin A). Tetrahetron Lett 1996, 37, 8581. <>
  • Paterson Ian, Gibson Karl R., Oballa Renata M.: Remote, 1,5-anti stereoinduction in the boron-mediated aldol reactions of β-oxygenated methyl ketones. Tetrahetron Lett 1996, 37, 8585. <>
  • González Ángel, Aiguadé Josep, Urpí Félix, Vilarrasa Jaume: Asymmetric acetate aldol reactions in connection with an enantioselective total synthesis of macrolactin A. Tetrahetron Lett 1996, 37, 8949. <>
  • Kernen Philippe, Vogel Pierre: Synthesis of Polypropionate Fragments Containing Tertiary-Alcohol Moieties. Cross-aldolisations with lithium enolates of 7-oxabicyclo[2.2.1]heptan-2-one derivatives. HCA 1995, 78, 301. <>
  • Brown Herbert C., Veeraraghavan Ramachandran P.: Versatile α-pinene-based borane reagents for asymmetric syntheses. J Organomet Chem 1995, 500, 1. <>
  • Paterson Ian, Cumming John G., Ward Richard A., Lamboley Serge: The total synthesis of swinholide A. Part 1: A stereocontrolled synthesis of a C19-C32 segment. Tetrahedron 1995, 51, 9393. <>
  • Paterson Ian, Ward Richard A., Smith Julian D., Cumming John G., Yeung Kap-Sun: The total synthesis of swinholide A. Part 3: A stereocontrolled synthesis of (−)-pre-swinholide A. Tetrahedron 1995, 51, 9437. <>
  • Paterson Ian, Bower Shelley, McLeod Malcolm D.: Stereocontrolled aldol additions to α-methylene-β-alkoxy aldehydes: Application to the synthesis of a C13C25 segment of bafilomycin A1. Tetrahedron Letters 1995, 36, 175. <>
  • Yadav J.S., Srinivas Rao C, Chandrasekhar S, Rama Rao A.V.: Asymmetric synthesis of C-19 to C-27 fragment of rifamycin-S. Tetrahetron Lett 1995, 36, 7717. <>
  • Chênevert Robert, Courchesne Gabriel: Enzymatic desymmetrization of meso(anti-anti)-2,4-dimethyl-1,3,5-pentanetriol. Tet Asymm 1995, 6, 2093. <>
  • Bernardi Anna, Gennari Cesare, Goodman Jonathan M., Paterson Ian: The rational design and systematic analysis of asymmetric aldol reactions using enol borinates: Applications of transition state computer modelling. Tet Asymm 1995, 6, 2613. <>
  • Paterson Ian, Franklin Alison S.: Assignment of the absolute configuration of the siphonarins and baconipyrones. Enantiocontrolled synthesis of a γ-pyrone subunit. Tetrahetron Lett 1994, 35, 6925. <>
  • Paterson Ian, Cumming John G., Smith Julian D., Ward Richard A.: Studies in marine macrolide synthesis: Boron and silicon-mediated coupling strategies for Swinholide A. Tetrahetron Lett 1994, 35, 441. <>
  • Paterson Ian, Wallace Debra J., Velázquez Silvia M.: Studies in polypropionate synthesis: High π-face selectivity in syn and anti aldol reactions of chiral boron enolates of lactate-derived ketones. Tetrahetron Lett 1994, 35, 9083. <>
  • Paterson Ian, Wallace Debra J.: Manipulation of the aldol adducts from lactate-derived ketones. A versatile chiral auxiliary for the asymmetric synthesis of β-hydroxy carbonyl compounds. Tetrahetron Lett 1994, 35, 9087. <>
  • Roush William R., Bannister Thomas D., Wendt Michael D.: Concerning the diastereofacial selectivity of aldol reactions of chiral methyl ketone enolates: Evidence for remote chelation in the bafilomycin aldol reaction. Tetrahetron Lett 1993, 34, 8387. <>
  • Paterson Ian, Kap-Sun Yeung: Studies in marine macrolide synthesis: A stereocontrolled synthesis of a C17-C32 subunit of scytophycin C. Tetrahetron Lett 1993, 34, 5347. <>
  • Paterson Ian, Tillyer Richard D., Ryan Glen R.: Studies in biomimetic polyether synthesis: Synthesis of an A-ring subunit of etheromycin. Tetrahedron Letters 1993, 34, 4389. <>