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Original Articles

Enantioselective Synthesis and Stereochemical Revision of Communiols A–C, Antibacterial 2,4-Disubstituted Tetrahydrofurans from the Coprophilous Fungus Podospora communis

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Pages 1921-1928 | Received 17 Mar 2008, Accepted 10 Apr 2008, Published online: 22 May 2014

  • 1) Che, Y., Gloer, J. B., Scott, J. A., and Malloch, D., Communiols A–D: new mono- and bis-tetrahydrofuran derivatives from the coprophilous fungus Podospora communis. Tetrahedron Lett., 45, 6891–6894 (2004).
  • 2) Che, Y., Araujo, A. R., Gloer, J. B., Scott, J. A., and Malloch, D., Communiols E–H: new polyketide metabolites from the coprophilous fungus Podospora communis. J. Nat. Prod., 68, 435–438 (2005).
  • 3) Ohtani, I., Kusumi, T., Kashman, Y., and Kakisawa, H., High-field FT NMR application of Mosher’s method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc., 113, 4092–4096 (1991).
  • 4) Bermejo, A., Figadère, B., Zafra-Polo, M.-C., Barrachina, I., Estornell, E., and Cortes, D., Acetogenins from Annonaceae: recent progress in isolation, synthesis and mechanisms of action. Nat. Prod. Rep., 22, 269–303 (2005).
  • 5) Wierenga, W., The total synthesis of ionophores. In “The Total Synthesis of Natural Products” Vol. 4, ed. ApSimon, J., Wiley, New York, pp. 263–351 (1981).
  • 6) Kuwahara, S., and Enomoto, M., Enantioselective synthesis and stereochemical revision of communiols A–C. Tetrahedron Lett., 46, 6297–6300 (2005).
  • 7) Enomoto, M., Nakahata, T., and Kuwahara, S., Stereochemical revision of communiols D and H through synthesis. Tetrahedron, 62, 1102–1109 (2006).
  • 8) Enomoto, M., and Kuwahara, S., Enantioselective total synthesis and stereochemical revision of communiols E and F. J. Org. Chem., 71, 6287–6290 (2006).
  • 9) Kolb, H. C., VanNieuwenhze, M. S., and Sharpless, K. B., Catalytic asymmetric dihydroxylation. Chem. Rev., 94, 2483–2547 (1994).
  • 10) Avedissian, H., Sinha, S. C., Yazbak, A., Sinha, A., Neogi, P., Sinha, S., and Keinan, E., Total synthesis of asimicin and bullatacin. J. Org. Chem., 65, 6035–6051 (2000).
  • 11) Sells, T. B., and Nair, V., Synthetic approaches to novel cis and trans dideoxynucleosides of the apiose family. Tetrahedron, 50, 117–138 (1994).
  • 12) Bouchard, H., Soulié, J., and Lallemand, J. Y., Towards the total synthesis of clerodin. Part II. Tetrahedron Lett., 32, 5957–5958 (1991).
  • 13) Odinokov, V. N., Vakhidov, R. R., Shakhmaev, R. N., and Zorin, V. V., Insect pheromones and their analogs. LIV. Synthesis of (E)-dodec-9-en-1-ol and its acetate, components of the sex pheromone of Sparganothis pilleriana. Khim. Prir. Soedin., 936–939 (1996).
  • 14) Bruyère, D., Bouyssi, D., and Balme, G., A study on the regio-and stereoselectivity in palladium-catalyzed cyclizations of alkenes and alkynes bearing bromoaryl and nucleophilic groups. Tetrahedron, 60, 4007–4017 (2004).
  • 15) Larchevêque, M., and Lalande, J., Les aminoacides précurseurs de synthons chiraux (IV) synthèse diastéréosélective d’α-diols énantiomériquement purs; préparation de la (+)-exobrévicomine. Bull. Soc. Chim. Fr., 116–122 (1987).
  • 16) Colin-Messager, S., Girard, J.-P., and Rossi, J.-C., Convenient method for the preparation of trityl ethers from secondary alcohols. Tetrahedron Lett., 33, 2689–2692 (1992).
  • 17) Kraus, G. A., Frazier, K. A., Roth, B. D., Taschner, M. J., and Neuenschwander, K., Conversion of lactones into ethers. J. Org. Chem., 46, 2417–2419 (1981).
  • 18) Brückner, C., Holzinger, H., and Reissig, H.-U., Diastereoselective syntheses of highly substituted methyl tetrahydrofuran-3-carboxylates by reactions of γ-lactols with silylated nucleophiles. J. Org. Chem., 53, 2450–2456 (1988).
  • 19) Carlsen, P. H. J., Katsuki, T., Martin, V. S., and Sharpless, K. B., A greatly improved procedure for ruthenium tetraoxide catalyzed oxidations of organic compounds. J. Org. Chem., 46, 3936–3938 (1981).
  • 20) Born, L., Lieb, F., Lorentzen, J. P., Moeschler, H., Nonfon, M., Söllner, R., and Wendisch, D., The relative configuration of acetogenins isolated from Annona squamosa; annonin I (squamocin) and annonin VI. Planta Med., 56, 312–316 (1990).
  • 21) Chávez, D., Acevedo, L. A., and Mata, R., Jimenezin, a novel annonaceous acetogenin from the seeds of Rollinia mucosa containing adjacent tetrahydrofuran–tetrahydropyran ring systems. J. Nat. Prod., 61, 419–421 (1998).
  • 22) Fujimoto, Y., Murasaki, C., Shimada, H., Nishioka, S., Kakinuma, K., Singh, S., Singh, M., Gupta, Y. K., and Sahai, M., Annonaceous acetogenins from the seeds of Annona squamosa. Non-adjacent bis-tetrahydrofuranic acetogenins. Chem. Pharm. Bull., 42, 1175–1184 (1994).
  • 23) Mitsunobu, O., The use of diethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis, 1–28 (1981).
  • 24) Martin, S. F., and Dodge, J. A., Efficacious modification of the Mitsunobu reaction for inversions of sterically hindered secondary alcohols. Tetrahedron Lett., 32, 3017–3020 (1991).
  • 25) Murga, J., Falomir, E., Carda, M., and Marco, J. A., Stereoselective synthesis of ent-communiols A–C. Tetrahedron Lett., 46, 8199–8202 (2005).
  • 26) Trost, B. M., and Zhang, T., Asymmetric synthesis of α-substituted aldehydes by Pd-catalyzed asymmetric allylic alkylation–alkene isomerization–Claisen rearrangement. Org. Lett., 8, 6007–6010 (2006).

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