Skip to main content
SpringerLink
Log in

Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

Aminohydroxylation of prochiral divinylcarbinol and subsequent Pd(II)-catalysed oxy-/amidocarbonylation of aminopentenediols is reported. The method was applied to the preparation of useful building blocks for syntheses of cytotoxic jaspines and glycosidase inhibitor DLX-homologues. The key intermediates, tetrahydrofuranolactones (l-arabino-II) and pyrrolidinolactones (l-arabino-IX and l-xylo-IX), were prepared in a short 2-step sequence from divinylcarbinol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • Abraham, E., Davies, S. G., Roberts, P. M., Russell, A. J., & Thomson, J. E. (2008). Jaspine B (pachastrissamine) and 2-epi-jaspine B: synthesis and structural assignment, Tetrahedron: Asymmetry, 19, 1027–1047. DOI: 10.1016/j.tetasy.2008.04.017.

    Article  CAS  Google Scholar 

  • Angelaud, R., Landais, Y., & Schenk, K. (1997). Asymmetric amino-hydroxylation of dienylsilanes. An efficient route to amino-cyclitols. Tetrahedron Letters, 38, 1407–1410. DOI: 10.1016/s0040-4039(97)00079-8.

    Article  CAS  Google Scholar 

  • Babjak, M., Kapitán, P., & Gracza, T. (2002). The first total synthesis of goniothalesdiol. Tetrahedron Letters, 43, 6983–6985. DOI: 10.1016/s0040-4039(02)01599-x.

    Article  CAS  Google Scholar 

  • Babjak, M., Kapitán, P., & Gracza, T. (2005). Synthesis of (+)-goniothalesdiol and (+)-7-epi-goniothalesdiol. Tetrahedron, 61, 2471–2479. DOI: 10.1016/j.tet.2005.01.004.

    Article  CAS  Google Scholar 

  • Bashyal, B. P., Fleet, G. W. J., Gough, M. J., & Smith, P. W. (1987). Synthesis of the α-Mannosidase inhibitors swainsonine[(1S,2R,8R,8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannose. Tetrahedron, 43, 3083–3093. DOI: 10.1016/s0040-4020(01) 86850-2.

    Article  CAS  Google Scholar 

  • Bhaket, P., Morris, K., Stauffer, C. S., & Datta, A. (2005). Total synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (jaspine B). Organic Letters, 7, 875–876. DOI: 10.1021/ol0473290.

    Article  CAS  Google Scholar 

  • Canals, D., Mormeneo, D., Fabriàs, G., Llebaria, A., Casas, J., & Delgado, A. (2009). Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines. Bioorganic & Medicinal Chemistry, 17, 235–241. DOI: 10.1016/j.bmc.2008.11.026.

    Article  CAS  Google Scholar 

  • Crimmins, M. T., Ellis, J. M., Emmitte, K. A., Haile, P. A., McDougall, P. J., Parrish, J. D., & Zuccarello, J. L. (2009). Enantioselective total synthesis of Brevetoxin A: Unified strategy for the B, E, G, and J subunits. Chemistry-A European Journal, 15, 9223–9234. DOI: 10.1002/chem.200900776.

    Article  CAS  Google Scholar 

  • Corey, E. J., Noe, M. C., & Guzman-Perez, A. (1995). Kinetic resolution by enantioselective dihydroxylation of secondary allylic 4-methoxybenzoate esters using a mechanistically designed cinchona alkaloid catalyst. Journal of the American Chemical Society, 117, 10817–10824. DOI: 10.1021/ja00149a004.

    Article  CAS  Google Scholar 

  • Dixon, D. J., Ley, S. V., Gracza, T., & Szolcsányi, P. (1999). Total synthesis of the polyenoyltetramic acid mycotoxin erythroskyrine. Journal of the Chemical Society, Perkin Transactions 1, 1999, 839–842. DOI: 10.1039/a809823i.

    Article  Google Scholar 

  • Enders, D., Terteryan, V., & Paleček, J. (2008). Asymmetric synthesis of jaspine B (pachastrissamine) via an organocatalytic aldol reaction as key step. Synthesis, 2008, 2278–2282. DOI: 10.1055/s-2008-1067142.

  • Fleet, G. W. J., Nicholas, S. J., Smith, P. W., Evans, S. V., Fellows, L. E., & Nash, R. J. (1985). Potent competitive inhibition of α-galactosidase and α-glucosidase activity by 1,4-dideoxy-1,4-iminopentitols: syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol and both enantiomers of 1,4-dideoxy-1,4-iminoarabinitol. Tetrahedron Letters, 26, 3127–3130. DOI: 10.1016/s0040-4039(00)98636-2.

    Article  CAS  Google Scholar 

  • Gracza, T., Hasenöhrl, T., Stahl, U., & Jäger, V. (1991). Synthesis of 3,5-anhydro-2-deoxy-1,4-glyconolactones by palladium (II)-catalyzed, regioselective oxycarbonylation of C5- and C6-enitols. ω-Homologation of aldoses to produce intermediates for C-glycoside/C-nucleoside synthesis. Synthesis, 1991, 1108–1118 DOI: 10.1055/s-1991-28400.

    Article  Google Scholar 

  • Gracza, T., & Jäger, V. (1992). Palladium(II)-catalyzed oxycarbonylation of unsaturated polyols: Synthesis of (−)-goniofufurone and assignment of absolute configuration to the natural (+)-enantiomer, a cytotoxic styryllactone. Synlett, 1992, 191–193. DOI: 10.1055/s-1992-21309.

    Article  Google Scholar 

  • Gracza, T., & Jäger, V. (1994). Synthesis of natural and unnatural enantiomers of goniofufurone and its 7-epimers from Dglucose. Application of palladium(II)-catalyzed oxycarbonylation of unsaturated polyols. Synthesis, 1994, 1359–1368. DOI: 10.1055/s-1994-25694.

    Article  Google Scholar 

  • Häfele, B., Schröter, D., & Jäger, V. (1986). SynSynthese von erythro-d- und l-4-Pententriolen; selektive Epoxyallylalkohol-hydrolyse unter Retention oder zweifacher Inversion (Enantiomerisierung). Angewandte Chemie, 98, 89–90. DOI: 10.1002/ange.19860980115.

    Article  Google Scholar 

  • Hümmer, W., Dubois, E., Gracza, T., & Jäger, T. (1997). Halocyclization and palladium(II)-catalyzed amidocarbonylation of unsaturated aminopolypols. Synthesis of 1,4-iminoglycitols as potential glycosidase inhibitors. Synthesis, 1997, 634–642. DOI: 10.1055/s-1997-3183.

    Article  Google Scholar 

  • Inuki, S., Yoshimitsu, Y., Oishi, S., Fujii, N., & Ohno, H. (2009). Ring-construction/stereoselective functionalization cascade: Total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of bromoallenes. Organic Letters, 11, 4478–4481. DOI: 10.1021/ol901904w.

    Article  CAS  Google Scholar 

  • Inuki, S., Yoshimitsu, Y., Oishi, S., Fujii, N., & Ohno, H. (2010). Ring-construction/stereoselective functionalization cascade: Total synthesis of pachastrissamine (jaspine B) through palladium-catalyzed bis-cyclization of propargyl chlorides and carbonates. The Journal of Organic Chemistry, 75, 3831–3842. DOI: 10.1021/jo100544v.

    Article  CAS  Google Scholar 

  • Jäger, V., & Hümmer, W. (1990). CCyclisierung N-geschützter 1-Amino-4-penten-2,3-diole zu lyxo-konfigurierten Desoxyiminozuckern (cis-Dihydroxypyrrolidinen); Synthese potentieller Glycosidase-Inhibitoren. Angewandte Chemie, 102, 1182–1183 DOI: 10.1002/ange.19901021022.

    Article  Google Scholar 

  • Jäger, V., Gracza, T., Dubois, E., Hasenöhrl, T., Hümmer, W., Kautz, U., Kirschbaum, B., Lieberknecht, A., Remeň, L., Shaw, D., Stahl, U., & Stephan, O. (1997). Pd(II)-catalyzed carbonylation of unsaturated polyols and aminopolyols. In G. Helmchen (Ed.), Proceedings of the Fifth Symposium Organic Synthesis via Organometallics (OSM5), September 26–28, 1996 (pp. 331–360). Braunschweig/Wiesbaden, Germany: Vieweg & Sohn Verlagsgesellschaft.

    Google Scholar 

  • Karlubíková, O., Babjak, M., & Gracza, T. (2011). Tetrahydropyran synthesis by palladium(II)-catalysed hydroxycarbonylation of hexenols: synthesis of (±)-diospongin A and (+)-civet cat compound. Tetrahedron, 67, 4980–4987. DOI: 10.1016/j.tet.2011.04.045.

    Article  Google Scholar 

  • Kuroda, I., Musman, M., Ohtani, I. I., Ichiba, T., Tanaka, J., Gravalos, D. G., & Higa, T. (2002). Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp. Journal of Natural Products, 65, 1505–1506. DOI: 10.1021/np010659y.

    Article  CAS  Google Scholar 

  • Ledroit, V., Debitus, C., Lavaud, C., & Massiot, G. (2003). Jaspines A and B: two new cytotoxic sphingosine derivatives from the marine sponge Jaspis sp. Tetrahedron Letters, 44, 225–228. DOI: 10.1016/s0040-4039(02)02541-8.

    Article  CAS  Google Scholar 

  • Li, G., Chang, H. T., & Sharpless, K. B. (1996). Catalytic asymmetric aminohydroxylation (AA) of olefins. Angewandte Chemie International Edition, 35, 451–454. DOI: 10.1002/anie.199604511.

    Article  CAS  Google Scholar 

  • Llaveria, J., Díaz, Y., Matheu, M. I., & Castillón, S. (2011). Enantioselective synthesis of jaspine B (pachastrissamine) and its C-2 and/or C-3 epimers. European Journal of Organic Chemistry, 2011, 1514–1519. DOI: 10.1002/ejoc.201001477.

  • Nicolaou, K. C., Rodríguez, R. M., Mitchell, H. J., & van Delft, F. L. (1998). Stereocontrolled synthesis of the everninomicin A1B(A)C ring framework. Angewandte Chemie International Edition, 37, 1874–1876. DOI: 10.1002/(SICI)1521-3773(19980803)37:13/14〈1874::AID-ANIE1874〉3.0.CO;2-K.

    Article  CAS  Google Scholar 

  • Passiniemi, M., & Koskinen, A. M. P. (2011). Asymmetric synthesis of Pachastrissamine (Jaspine B) and its diastereomers via η 3-allylpalladium intermediates. Organic & Biomolecular Chemistry, 99, 1774–1783. DOI: 10.1039/c0ob00643b.

    Article  Google Scholar 

  • Reddy, K. L., & Sharpless, K. B. (1998). From styrenes to enantiopure α-arylglycines in two steps. Journal of the American Chemical Society, 120, 1207–1217. DOI: 10.1021/ja9728177.

    Article  CAS  Google Scholar 

  • Romero, A., & Wong, C. H. (2000). Chemo-enzymatic total synthesis of 3-epiaustraline, australine, and 7-epialexine. The Journal of Organic Chemistry, 65, 8264–8268. DOI: 10.1021/jo000933d.

    Article  CAS  Google Scholar 

  • Salma, Y., Ballereau, S., Maaliki, C., Ladeira, S., Andrieu-Abadie, N., & Génisson, Y. (2010). Flexible and enantioselective access to jaspine B and biologically active chainmodified analogues thereof. Organic & Biomolecular Chemistry, 8, 3227–3243. DOI: 10.1039/c004218h.

    Article  CAS  Google Scholar 

  • Schreiber, S. L., Schreiber, T. S., & Smith, D. B. (1987). Reactions that proceed with a combination of enantiotopic group and diastereotopic face selectivity can deliver products with very high enantiomeric excess: experimental support of a mathematical model. Journal of the American Chemical Society, 109, 1525–1529. DOI: 10.1021/ja00239a036.

    Article  CAS  Google Scholar 

  • Singh, S., & Guiry, P. J. (2009). Microwave-assisted synthesis of substituted tetrahydropyrans catalyzed by ZrCl4 and its application in the asymmetric synthesis of exo- and endobrevicomin. The Journal of Organic Chemistry, 74, 5758–5761. DOI: 10.1021/jo901019u.

    Article  CAS  Google Scholar 

  • Srinivas Rao, G., & Venkateswara Rao, B. (2011). A common strategy for the stereoselective synthesis of anhydrophytosphingosine pachastrissamine (jaspine B) and N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine. Tetrahedron Letters, 52, 6076–6079. DOI: 10.1016/j.tetlet.2011.08.170.

    Article  CAS  Google Scholar 

  • Tao, B., Schlingloff, G., & Sharpless, K. B. (1998). Reversal of regioselection in the asymmetric aminohydroxylation of cinnamates. Tetrahedron Letters, 39, 2507–2510. DOI: 10.1016/s0040-4039(98)00350-5.

    Article  CAS  Google Scholar 

  • Urano, H., Enomoto, M., & Kuwahara, S. (2010). Enantioselective syntheses of pachastrissamine and jaspine A via hydroxylactonization of a chiral epoxy ester. Bioscience, Biotechnology, and Biochemistry, 74, 152–157. DOI: 10.1271/bbb.90670.

    Article  CAS  Google Scholar 

  • Vichare, P., & Chattopadhyay, A. (2010). Nitrolaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde: a simple and stereoselective synthesis of the cytotoxic Pachastrissamine (Jaspine B). Tetrahedron: Asymmetry, 21, 1983–1987. DOI: 10.1016/j.tetasy.2010.06.024.

    Article  CAS  Google Scholar 

  • Yoshimitsu, Y., Inuki, S., Oishi, S., Fujii, N., & Ohno, H. (2010). Stereoselective divergent synthesis of four diastereomers of pachastrissamine (jaspine B). The Journal of Organic Chemistry, 75, 3843–3846. DOI: 10.1021/jo1005284.

    Article  CAS  Google Scholar 

  • Yoshimitsu, Y., Oishi, S., Miyagaki, J., Inuki, S., Ohno, H., & Fujii, N. (2011). Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C. Bioorganic & Medicinal Chemistry, 19, 5402–5408. DOI: 10.1016/j.bmc.2011.07.061.

    Article  CAS  Google Scholar 

  • Wang, H., Matsuhashi, H., Doan, B. D., Goodman, S. N., Ouyang, X., & Clark, W. M., Jr. (2009). Large-scale synthesis of SB-462795, a cathepsin K inhibitor: the RCM-based approaches. Tetrahedron, 65, 6291–6303. DOI: 10.1016/j.tet.2009.06.022.

    Article  CAS  Google Scholar 

  • Winkler, D. A., & Holan, G. (1989). Design and potential anti-HIV agents. 1. Mannosidase inhibitors. Journal of Medicinal Chemistry, 32, 2084–2089. DOI: 10.1021/jm00129a011.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Oľga Caletková, Diana Ďurišová & Tibor Gracza

  2. Central NMR Laboratories, Faculty of Chemical and Food Technology, Slovak University of Technology, Radlinského 9, 812 37, Bratislava, Slovakia

    Naďa Prónayová

Authors
  1. Oľga Caletková
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Diana Ďurišová
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Naďa Prónayová
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Tibor Gracza
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tibor Gracza.

Additional information

Dedicated to Professor Štefan Toma on the occasion of his 75th birthday

Rights and permissions

Reprints and permissions

About this article

Cite this article

Caletková, O., Ďurišová, D., Prónayová, N. et al. Aminohydroxylation of divinylcarbinol and its application to the synthesis of bicyclic hydroxypyrrolidine and aminotetrahydrofuran building blocks. Chem. Pap. 67, 66–75 (2013). https://doi.org/10.2478/s11696-012-0224-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-012-0224-5

Keywords

Search

Navigation