연구동향 분석
박사

1. Stereoselective Total Syntheses of (-)-1-Deoxygulonojirimycin and N-Acetylneuraminic Acid via Chiral 1,3-Oxazine 2. Stereoselective Allylation of α-Hydroxy Aldimine and Formal Synthesis of (-)-β-Conhydrine

이용택 2018년

논문상세정보
인용/피인용
' 1. Stereoselective Total Syntheses of (-)-1-Deoxygulonojirimycin and N-Acetylneuraminic Acid via Chiral 1,3-Oxazine 2. Stereoselective Allylation of α-Hydroxy Aldimine and Formal Synthesis of (-)-β-Conhydrine' 의 주제별 논문영향력
논문영향력 선정 방법
논문영향력 요약
주제
  • Polyhydroxylated alkaloids
  • chiral building block
  • stereoselective nucleophilic addition
  • total synthesis
동일주제 총논문수 논문피인용 총횟수 주제별 논문영향력의 평균
17 0

0.0%

' 1. Stereoselective Total Syntheses of (-)-1-Deoxygulonojirimycin and N-Acetylneuraminic Acid via Chiral 1,3-Oxazine 2. Stereoselective Allylation of α-Hydroxy Aldimine and Formal Synthesis of (-)-β-Conhydrine' 의 참고문헌

  • von Itzstein, M. et al. Nature 1993, 363, 418–423.
  • Yoon, Y. J., Joo, J. E., Lee, K. Y., Kim, Y. H., Oh, C. Y., Ham, W. H. Tetrahedron Lett.2005, 46, 739-741.
  • Wani, M. C., Taylor, H. L., Wall, M. E., Coggon, P., McPhail, A. T. J. Am. Chem. Soc.1971, 93, 2325-2327.
  • Umezawa, H.; Aoyagi, T.; Suda, H.; Hamada, M.; Takeuchi, T. J. Antibiot. 1976, 29, 97–99.
  • Spa th, E.; Adler, E. Zur Konstitution des Konhydrins. Monatsh. Chem. 1933, 63, 127–140.
  • Singh, A.; Kim, B.; Lee, W. K.; Ha, H. J. Org. Biomol. Chem. 2011, 9, 1372–1380.
  • Savi, C. D.; Watson, K.; Banwell, M. J. Chem. Soc., Perkin Trans. 1, 1998, 2251–2252
  • Saksena, A. K.; Girijavallabhan, V. M.; Wang, H.; Lovey, R. G.; Guenter, F.; Mergelsberg, I.; Puar, M. S. Tetrahedron Lett. 2004, 45, 8249–8251.
  • Reyes, E.; Ruiz, N.; Vicario, J. L.; Bad a, D.; Carrillo, L. Synthesis 2011, 3, 443–450.
  • Reetz, M. T.; Jaeger, R.; Drewlies, R.; H bel, M.; Angew. chem. int. ed. engl. 1991, 30, 103–106.
  • Pyun, S. J., Lee, K. Y., Oh, C. Y., Joo, J. E., Cheon, S. H., Ham, W. H. Tetrahedron 2005, 61, 1413-1416.
  • Pyun, S. J., Lee, K. Y., Oh, C. Y., Ham, W. H. Heterocycles 2004, 62, 333-341.
  • Pham, V. T., Joo, J. E., Lee, K. Y., Kim, T. W., Mu, Y., Ham, W. H. Tetrahedron, 2010, 66, 2123- 2131.
  • Park, S. H.; Kim, J. Y.; Kim, J. S.; Jung, C. Y.; Song, D. K.; Ham, W. H. Tetrahedron: Asymmetry 2015, 26, 657–661.
  • Park, S. H.; Jin, X. D.; Kang, J. C.; Jung, C. Y.; Kim, S. S.; Kim, S. S.; Lee, K. Y.; Ham, W. H. Org. Biomol. Chem. 2015, 13, 4539–4550.
  • Omura, S., Imamura, N., Kawakita, K., Mori, Y., Yamazaki, Y., Masuma, R., Takahashi, Y., Tanaka, H., Huang, L-Y., Woodruff, H. B. J. Antibiot.1986, 39, 1079-1085.
  • Myeong, I. S.; Kim, J. S.; Lee, Y. T.; Kang, J. C.; Park, S. H.; Jung, C. Y.; Ham, W. H. Tetrahedron: Asymmetry 2016, 27, 823–828.
  • Myeong I. S.; Lee Y. T.; Lee S. H.; Jung C.; Kim J. S.; Park S. H.; Kang J.; Lee S. J.; Ye I. H.; Ham W. H. Tetrahedron: Asymmetry 2017, 28, 1053–1060.
  • Mu, Y., Jin, T., Kim, G. W., Kim, J. S., Kim, S. S., Tian, Y. S., Oh, C. Y., Ham, W. H. Eur. J. Org. Chem. 2012, 2614-2620.
  • Menche, D.; Arikan, F.; Li, J.; Rudolph, S. Org. Lett. 2007, 9, 267–270.
  • Lorpitthaya, R.;Suryawanshi, S. B.; Wang, S.; Pasunooti, K. K.; Cai, S.; Ma, J.; Liu, X. W. Angew. Chem. Int. Ed. 2011, 50, 12054–12057.
  • Liu, K. G.; Yan, S.; Wu, Y. L.; Yao, Z. J. Org. Lett. 2004, 6, 2269–2272.
  • Liu, K. G.; Yan, S.; Wu, Y. L.; Yao, Z. J. J. Org. Chem. 2002, 67, 6758–6763.
  • Lee, Y. S.; Shin, Y. H.; Kim, Y. H.; Lee, K. Y.; Oh, C. Y.; Pyun, S. J.; Park, H. J.; Jeong, Y. H.; Ham, W. H. Tetrahedron: Asymmetry 2003, 14, 87–93.
  • Lee, K. Y.; Oh, C. Y.; Kim, Y. H.; Joo, J. E.; Ham, W. H. Tetrahedron Lett. 2002, 43, 9361–9363.
  • Lee, K. Y.; Oh, C. Y.; Ham, W. H. Org. Lett. 2002, 4, 4403–4405.
  • Lee, K. Y.; Kim, Y. H.; Oh, C. Y.; Ham, W. H. Org. Lett. 2000, 2, 4041–4042.
  • Kumar, J. N.; Reddy, P. R.; Das, B.; Kumar, C. G.; Sujitha, P. Bioorg. Med. Chem. Lett. 2013, 23, 5192–5194.
  • Kim, J. Y., Mu, Y., Jin, X., Park, S. H., Pham, V. T., Song, D. K., Lee, K. Y., Ham, W. H. Tetrahedron2011, 67, 9426-9432.
  • Kim, J. S.; Lee, Y. T.; Lee, K. H.; Myeong, I. S.; Kang, J. C.; Jung, C. Y.; Park, S. H.; Ham, W. H. J. Org. Chem. 2016, 81, 7432–7438
  • Kim, J. S., Kang, J. C., Yoo, G. H., Jin, X., Myeong, I. S., Oh, C. Y., Ham, W. H. Tetrahedron 2015, 71, 2772-2776.
  • Kim, G. W., Jin, T., Kim, J. S., Park, S. H., Lee, K. H., Kim, S. S., Myeong, I. S., Ham, W. H. Tetrahedron: Asymmetry 2014, 25, 87-91.
  • Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem. Soc. 1997, 119, 681–690.
  • Joo, J. E., Lee, K. Y., Pham, V. T., Tian, Y. S., Ham, W. H. Org. Lett.2007, 9, 3627-3630.
  • Johann, M.; Angermann, A.; Muench, W. Liebigs Ann. Chem. 1986, 825–838.
  • Ishimaru, K.; Tsuru, K.; Yabuta, K.; Wada, M.; Yamamoto, Y.; Akiba, K. Tetrahedron 1996, 52, 13137–13144.
  • Iizuka, K., Kamijo, T., Kubota, T., Akahane, K., Umeyama, H., Kiso, Y. J. Med. Chem.1988, 31, 704-706.
  • Iizuka, K., Kamijo, T., Harada, H., Akahane, K., Kubota, T., Umeyama, H., Kiso, Y. J. Chem. Soc., Chem. Commun.1989, 1678-1680.
  • Horne, G.; Wilson, F. X.; Tinsley, J.; Williams, D. H.; Storer, R. Drug Discovery Today 2011, 16, 107–118.
  • Hong, Z.; Liu, L.; Hsu, C. C.; Wong, C. H. Angew. Chem. Int. Ed. 2006, 45, 7417–7421.
  • Gung. B. W. In Additions of Allyl, Allenyl, and Propargylstannanes to Aldehydes and Imines: Overman L. E., Ed., Organic Reactions, Vol. 64, Chap. 1, John Wiley & Sons, Inc., New Jersey, 2004, p 1.
  • Furukawa, K.; Shibuya, M.; Yamamoto, Y. Org. Lett. 2015, 17, 2282–2285.
  • For selected reviews: (a) Reets, M. T. Angew. Chem. Int. Ed. Engl. 1984, 23, 556–569. (b) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462–468. (c) Yamamoto, Y., Asao, N. Chem. Rev. 1993, 93, 2207– 2293. (d) Mengel, A., Reiser, O. Chem. Rev. 1999, 99, 1191–1223. (e) Yus, M., Gonz lez-G mez, J. C., Foubelo, F. Chem. Rev. 2013, 113, 5595–5698.
  • For reviews: (a) Jurczak, J., Golebiowski, A. Chem. Rev. 1989, 89, 149–164. (b) Reetz, M. R. Angew. Chem. Int. Ed. Engl. 1991, 30, 1531–1546. (c) Marshall, J. A. Chem. Rev. 1996, 96, 31–47. (d) Reetz, M. R. Chem. Rev. 1999, 99, 1121–1162. (e) Bergmeier, S. C. Tetrahedron 2000, 56, 2561–2576. (f) Liang, X., Andersch, J., Bols, M. J. Chem. Soc., Perkin Trans 1 2001, 2136–2157. (g) Hili, R., Baktharaman, S., Yudin, A. K. Eur. J. Org. Chem. 2008, 5201–5213. (h) Karjalainen, O. K., Koskinen, A. M. P. Org. Biomol. Chem. 2012, 10, 4311–4326. (i) Passiniemi, M., Koskinen, A. M. P. Beilstein J. Org. Chem. 2013, 9, 2641–2659.
  • Evans, J. W.; Ellman, J. A. J. Org. Chem. 2003, 68, 9948–9957.
  • DeNinno, M. P.; Danishefsky, S. J. J. Org. Chem. 1986, 51, 2617–2618.
  • Cornforth, J. W.; Firth, M. E.; Gottschalk, A. Biochem. J. 1958, 68, 57–61.
  • Compain, P.; Chagnault, V.; Martin, O. R. Tetrahedron: Asymmetry 2009, 20, 672–711.
  • Choi, H. W.; Kim, J. S.; Youn J. H.; Kang, S. H. Chem. Commun. 2000, 227–228.
  • Chan, T. H.; Chang, Y. F.; Hsu, J. J.; Cheng, W. C. Eur. J. Org. Chem. 2010, 29, 5555–5559.
  • Bressel, B.; Reissig, H. U. Org. Lett. 2009, 11, 527–530.
  • Bloch, R. Chem. Rev. 1998, 98, 1407–1438.
  • Aoyagi, T.; Tobe, H.; Kojima, F.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1978, 31, 636–639.
  • Amat, M.; Huguet, M.; Llor, N.; Bassas, O.; Gómez, A. M.; Bosch, J.; Badia, J.; Baldoma, L.; Aguilar, J. Tetrahedron Lett. 2004, 45, 5355–5356.
  • Abrecht, S.; Harrington, P.; Iding, H.; Karpf, M.; Trussardi, R.; Wirz, B.; Zutter, U. Chimia 2004, 58, 621–629.
  • (a) Yamamoto, Y.; Komatsu, T.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1985, 814–816; (b) Claremon, D. A.; Lumma, P. K.; Phillips, B. T. J. Am. Chem. Soc. 1986, 108, 8265–8266; (c) Franz, T.; Hein, M.; Veith, U.; Jager, V.; Peters, E. M.; Peters, K. Schnering, H. G. Angew. Chem. 1994, 106, 1308–1311; (d) Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450–1456; (e) Tronchet, J. M. J.; Balkadjian, M.; Zosimo-Landolfo, G.; Barbalat-Rey, F.; Lichtle, P.; Ricca, Al.; Komaromi, I.; Bernardinelli, G.; Geoffroy, M. J. Carbohyd. Chem. 1995, 14, 17–34; (f) Merino, P.; Anoro, S.; Castillo, E.; Merchan, F.; Tejero, T. Tetrahedron: Asymmetry 1996, 7, 1887–1890; (g) Veith, U.; Schwardt, O.; Jager, V. Synlett 1996, 1181–1183.
  • (a) Von Itzstein, M.; Wu, W. Y.; Chandler, M. Carbohydr. Res. 1993, 244, 181–185; (b) Scheigetz, J.; Zamboni, R.; Bernstein, M. A.; Roy, B. Org. Prep. Proc. Int. 1995, 27, 637–644.
  • (a) Venkataiah, M.; Rao, B. V.; Fadnavis, N. W. Tetrahedron: Asymmetry 2009, 20, 198–201; (b) Venkataiah, M.; Fadnavis, N. W. Tetrahedron 2009, 65, 6950–6952.
  • (a) Umezawa, H., Aoyagi, T., Morishima, H., Matsuzaki, M., Hamada, M., Takeuchi, T. J. Antibiot.1970, 23, 259-262, (b) Babine, R. E., Bender, L. E. Chem. Rev.1997, 97, 1359-1472.
  • (a) Tomioka, K.; Inoue, I.; Shindo, M.; Koga, K. Tetrahedron Lett. 1990, 31, 6681–6684; (b) Inoue, I.; Shindo, M.; Koga, K.; Tomioka, K. Tetrahedron: Asymmetry 1993, 4, 1603–1606.
  • (a) Scott, L. J.; Spencer, C. M. Drugs 2000, 59, 521−549. (b) Machaczka, M.; Klimkowska, M.; Hagglund, H. Adv. Med. Sci. 2012, 57, 169–173.
  • (a) Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem. 1987, 99, 1186-1188; (b) Herold, P. Helv. Chim. Acta 1988, 71, 354–362; (c) Schirilin, D.; Baltzer, S.; Altenburger, J. M. Tetrahedron Lett. 1988, 29, 3687–3690; (d) Reetz, M. T. Pure Appl. Chem. 1988, 60, 1607–1614; (e) Reetz, M. T.; R lfing, K.; Griebenow, N. Tetrahedron Lett. 1994, 35, 1969–1972.51 Salma, Y.; Ballereau, S.; Maaliki, C.; Ladeira, S.; Andrieu-Ababie, N.; G nisson, Y. Org. Biomol. Chem. 2010, 8, 3227–3243.
  • (a) Lindsay, V.N.G.; Charette, A.B. in Comprehensive Organic Synthesis II, 2nd ed. (Eds.: Knochel, P; Molander, G.A.), Elsevier, Oxford, 2014, pp. 365–394; (b) Marcantoni, E.; Petrini, M. in Comprehensive Organic Synthesis II, 2nd ed. (Eds.: Knochel, P; Molander, G.A.), Elsevier, Amsterdam, 2014, pp. 344–364.
  • (a) Jager, V.; Muller, I. Tetrahedron 1985, 41, 3519–3528; (b) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1987, 746–748; (c) Miller, V. P.; Yang, D.; Weigel, T. M.; Han, O.; Liu, H. J. Org. Chem. 1989, 54, 4175–4188; (d) Williams, D. R.; Osterhout, M. H.; Reddy, J. Tetrahdron Lett. 1993, 34, 3271–3274; (e) Banaszek, A.; Karpiesiuk, W. Carbohydr. Res. 1994, 251, 233–242; (f) Shimizu, M.; Tsukamoto, K.; Fujisawa, T. Tetrahedron Lett. 1997, 38, 5193– 5196; (g) Alonso, E.; Ramon, D. J.; Yus, M. Tetrahedron 1998, 54, 12007–12028.
  • (a) Fukasawa, T.; Takeuchi, T.; Aoyagi, T. Umezawa, H. J. Antibiot. 1980, 33, 642–652; (b) Umezawa, H., Ed. Small Molecular Immunomodifiers of Microbial Origin. Fundamental and Clinical Studies of Bestatin; Pergamon Press: Oxford, 1981; (c) Miura, K.; Sawa, T.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1986, 34, 734–746; (d) Okura, A.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 1988, 41, 261–263; (e) Blomgren, H.; Wasserman, J. Cancer Lett. 1981, 11, 303–308; (f) Nishizawa, R.; Saino, T.; Takita, T.; Suda, H.; Aoyagi, T.; Umezawa, H. J. Med. Chem. 1977, 20, 510–515; (g) Rich, D. H.; Jo Moon, B. Boparai, A. S. J. Org. Chem. 1980, 45, 2288–2290.
  • (a) Cainelli, G.; Giacomini, D.; Trer , A.; Galletti, P. Tetrahedron: Asymmetry 1995, 6, 1593– 1600; (b) Cainelli, G.; Giacomini, D.; Panunzio, M.; Zarantonello, P. Tetrahedron Lett. 1992, 33, 7783–7786.
  • (a) Alcaide, B.; Dominguez, G.; Lopez-Mardoningo, C.; Perez-Ossorio, R.; Plumet, J. J. Chem. Soc., Perkin Trans. II 1986, 99–103; (b) Dufour, M. N.; Jouin, P.; Poncet, J.; Pantaloni, A.; Castro, B. J. Chem. Soc. Perkin Trans. I 1986, 1895–1899; (c) Maibaum, J.; Rich, D. H. J. Org. Chem. 1988, 53, 869–873; (d) Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866– 1875; (e) Dondoni, A.; Perrone, D. Synthesis 1993, 1162–1176; (f) Chung, S. K.; Kang, D. H. Tetrahedron: Asymmetry 1997, 8, 3027–3030; (g) Hoffman, R. V.; Tao, J. J. Org. Chem. 1997, 62, 2292–2297; (h) Ballini, R.; Bosica, G.; Marcantoni, E.; Vita, P. J. Org. Chem. 2000, 65, 5854– 5857; (i) Hoffman, R. V.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045–1056.