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

[1] 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. http://dx.doi.org/10.1016/j.tetasy.2008.04.01710.1016/j.tetasy.2008.04.017Search in Google Scholar

[2] 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. http://dx.doi.org/10.1016/S0040-4039(97)00079-810.1016/S0040-4039(97)00079-8Search in Google Scholar

[3] 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. http://dx.doi.org/10.1016/S0040-4039(02)01599-X10.1016/S0040-4039(02)01599-XSearch in Google Scholar

[4] 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. http://dx.doi.org/10.1016/j.tet.2005.01.00410.1016/j.tet.2005.01.004Search in Google Scholar

[5] 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. http://dx.doi.org/10.1016/S0040-4020(01)86850-210.1016/S0040-4020(01)86850-2Search in Google Scholar

[6] 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. http://dx.doi.org/10.1021/ol047329010.1021/ol0473290Search in Google Scholar PubMed

[7] 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. http://dx.doi.org/10.1016/j.bmc.2008.11.02610.1016/j.bmc.2008.11.026Search in Google Scholar PubMed

[8] 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. http://dx.doi.org/10.1002/chem.20090077610.1002/chem.200900776Search in Google Scholar PubMed PubMed Central

[9] 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. http://dx.doi.org/10.1021/ja00149a00410.1021/ja00149a004Search in Google Scholar

[10] 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. http://dx.doi.org/10.1039/a809823i10.1039/a809823iSearch in Google Scholar

[11] 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. 10.1055/s-2008-1067142Search in Google Scholar

[12] 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. http://dx.doi.org/10.1016/S0040-4039(00)98636-210.1016/S0040-4039(00)98636-2Search in Google Scholar

[13] 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. http://dx.doi.org/10.1055/s-1991-2840010.1055/s-1991-28400Search in Google Scholar

[14] 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. http://dx.doi.org/10.1055/s-1992-2130910.1055/s-1992-21309Search in Google Scholar

[15] 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. http://dx.doi.org/10.1055/s-1994-2569410.1055/s-1994-25694Search in Google Scholar

[16] 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. http://dx.doi.org/10.1002/ange.1986098011510.1002/ange.19860980115Search in Google Scholar

[17] 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. http://dx.doi.org/10.1055/s-1997-318310.1055/s-1997-3183Search in Google Scholar

[18] 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. http://dx.doi.org/10.1021/ol901904w10.1021/ol901904wSearch in Google Scholar PubMed

[19] 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. http://dx.doi.org/10.1021/jo100544v10.1021/jo100544vSearch in Google Scholar PubMed

[20] 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. http://dx.doi.org/10.1002/ange.1990102102210.1002/ange.19901021022Search in Google Scholar

[21] 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. Search in Google Scholar

[22] 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. http://dx.doi.org/10.1016/j.tet.2011.04.04510.1016/j.tet.2011.04.045Search in Google Scholar

[23] 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. http://dx.doi.org/10.1021/np010659y10.1021/np010659ySearch in Google Scholar

[24] 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. http://dx.doi.org/10.1016/S0040-4039(02)02541-810.1016/S0040-4039(02)02541-8Search in Google Scholar

[25] 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. http://dx.doi.org/10.1002/anie.19960451110.1002/anie.199604511Search in Google Scholar

[26] 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. 10.1002/ejoc.201001477Search in Google Scholar

[27] 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. http://dx.doi.org/10.1002/(SICI)1521-3773(19980803)37:13/14<1874::AID-ANIE1874>3.0.CO;2-K10.1002/(SICI)1521-3773(19980803)37:13/14<1874::AID-ANIE1874>3.0.CO;2-KSearch in Google Scholar

[28] 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. http://dx.doi.org/10.1039/c0ob00643b10.1039/c0ob00643bSearch in Google Scholar

[29] 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. http://dx.doi.org/10.1021/ja972817710.1021/ja9728177Search in Google Scholar

[30] 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. http://dx.doi.org/10.1021/jo000933d10.1021/jo000933dSearch in Google Scholar

[31] 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. http://dx.doi.org/10.1039/c004218h10.1039/c004218hSearch in Google Scholar

[32] 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. http://dx.doi.org/10.1021/ja00239a03610.1021/ja00239a036Search in Google Scholar

[33] 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. http://dx.doi.org/10.1021/jo901019u10.1021/jo901019uSearch in Google Scholar

[34] 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. http://dx.doi.org/10.1016/j.tetlet.2011.08.17010.1016/j.tetlet.2011.08.170Search in Google Scholar

[35] 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. http://dx.doi.org/10.1016/S0040-4039(98)00350-510.1016/S0040-4039(98)00350-5Search in Google Scholar

[36] 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. http://dx.doi.org/10.1271/bbb.9067010.1271/bbb.90670Search in Google Scholar PubMed

[37] 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. http://dx.doi.org/10.1016/j.tetasy.2010.06.02410.1016/j.tetasy.2010.06.024Search in Google Scholar

[38] 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. http://dx.doi.org/10.1021/jo100528410.1021/jo1005284Search in Google Scholar PubMed

[39] 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. http://dx.doi.org/10.1016/j.bmc.2011.07.06110.1016/j.bmc.2011.07.061Search in Google Scholar PubMed

[40] 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. http://dx.doi.org/10.1016/j.tet.2009.06.02210.1016/j.tet.2009.06.022Search in Google Scholar

[41] 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. http://dx.doi.org/10.1021/jm00129a01110.1021/jm00129a011Search in Google Scholar PubMed