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Recent Development for Stereoselective Synthesis of 1,3-Polyol

Recent Development for Stereoselective Synthesis of 1,3-Polyol. Ye Zhu Prof. Burgess’ Group Aug. 19, 2010. Introduction. The 1,3-polyol structure cluster is present in numerous natural products ranging from antibiotics to marine natural products. A substructure

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Recent Development for Stereoselective Synthesis of 1,3-Polyol

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  1. Recent Development for Stereoselective Synthesis of 1,3-Polyol Ye Zhu Prof. Burgess’ Group Aug. 19, 2010

  2. Introduction The 1,3-polyol structure cluster is present in numerous natural products ranging from antibiotics to marine natural products. A substructure search with SciFinder gave 87 and 35 natural products bearing one or more of 1,3,5,7,9-pentaol(s) and 1,3,5,7,9,11,13-heptaol(s), respectively.

  3. Introduction Michael, Muller, et al, Synthesis, 2006, 557.

  4. Introduction C-C Bond Forming Reactions Asymmetric Alkylation Knochel, P., et al, Tetrahedron Lett., 1993, 5881.

  5. Introduction C-C Bond Forming Reactions Asymmetric Allylation advantage: allylation can be carried out iteratively easily Leighton, J.L. et al, Angew. Chem. Int. Ed. 2003, 946.

  6. Introduction C-C Bond Forming Reactions Reagent Controlled Aldol Reaction Mahler, U., et al, Chem. Ber. 1988, 2035.

  7. Introduction Stereoselective Reduction Directed Reduction of β-Hydroxyketones

  8. Introduction Stereoselective Reduction Asymmetric Hydrogenation Uchida Y.. et al, Tetrahedron1993, 1997.

  9. Introduction Homoallylic Alcohol As Substrate Asymmetric Silylformylation Leighton, J.L. et al, J. Am. Chem. Soc. 2000, 122, 8587.

  10. Catalytic Asymmetric Overman Esterification Overman, L.E.; et al, J. Am. Chem. Soc. 2005, 2866. Kirsch, S.F., et al, Chem. Commun.., 2007, 4164. Kirsch, S.F., et al, Chem. Commun.., 2007, 4164. Kirsch, S.F., et al, Org. Lett., 2009, 5634.

  11. 1,3-anti-Diols Through Catalytic Hydrogenations Genet J.P., et al, Org. Lett., 2007, 105.

  12. Iterative Cr-Mediated Catalytic Asymmetric Allylation Kishi, Y., et al, Org. Lett., 2008, 3073. Kishi, Y., et al, Org. Lett., 2008, 3077.

  13. Iterative Cr-Mediated Catalytic Asymmetric Allylation Kishi, Y., et al, Org. Lett., 2008, 3073. Kishi, Y., et al, Org. Lett., 2008, 3077.

  14. Proline-Catalyzed Sequential α-Aminoxylation and Horner-Wadsworth-Emmons Olefination of Aldehydes Kumar, P., et al, Org. Lett., 2009, 2611.

  15. Iridium-Catalyzed Enantioselective Carbonyl Allylation and Iterative Two-Directional Assembly of 1,3-Polyols Krische, M. J. et al, Angew. Chem. Int. Ed., 2009, 5018.

  16. Elongation of 1,3-Polyols via Iterative Catalyst-Directed Carbonyl Allylation from the Alcohol Oxidation Level Krische, M. J. et al, Org. Lett., 2009, 3112.

  17. Elongation of 1,3-Polyols via Iterative Catalyst-Directed Carbonyl Allylation from the Alcohol Oxidation Level Krische, M. J. et al, Org. Lett., 2009, 3112.

  18. Elongation of 1,3-Polyols via Iterative Catalyst-Directed Carbonyl Allylation from the Alcohol Oxidation Level

  19. Iridium-Catalyzed Enantioselective Carbonyl Allylation and Iterative Two-Directional Assembly of 1,3-Polyols Krische, M. J. et al, Angew. Chem. Int. Ed., 2009, 5018.

  20. Iridium-Catalyzed Enantioselective Carbonyl Allylation and Iterative Two-Directional Assembly of 1,3-Polyols Krische, M. J. et al, Angew. Chem. Int. Ed., 2009, 5018.

  21. Direct Catalytic Asymmetric Aldol Reactions of Thioamides: Toward a Stereocontrolled Synthesis of 1,3-Polyols Shibasaki, M. et al, J. Am. Chem.Soc., 2009, 18244.

  22. Direct Catalytic Asymmetric Aldol Reactions of Thioamides: Toward a Stereocontrolled Synthesis of 1,3-Polyols Shibasaki, M. et al, J. Am. Chem.Soc., 2009, 18244.

  23. STEREOCHEMISTRY OF ALTERNATING POLYOL CHAINS: 13C NMR ANALYSIS OF 1,3-DIOL ACETONIDES Rycbnovsky, S.D., et al, Tetrahedron Lett., 1990, 945

  24. Rycbnovsky, S.D., et al, Tetrahedron Lett., 1990, 945

  25. Thanks

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