Synthesis of castanospermine

Tetrahedron

Volumn 64, Issue 12, 2008, Pages 2725-2732

  Machan, Theeraphan ^a,b   Davis, Andrew S ^a   Liawruangrath, Boonsom ^b   Pyne, Stephen G ^a  

^a UNIVERSITY OF WOLLONGONG   (Australia)

^b CHIANG MAI UNIVERSITY   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLAMINE; BORONIC ACID DERIVATIVE; CASTANOSPERMINE; KETONE DERIVATIVE; PYRROLO[1,2 C]OXAZOL 3 ONE; STYRENE; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGENOLYSIS; HYDROLYSIS; HYDROXYLATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 39149142197     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.073     Document Type: Article

References (85)

1. Hohenschutz L.D., Bell E.A., Jewess P.J., Leworth D.P., Pryce R.J., Arnold E., and Clardy J. Phytochemistry 20 (1981) 811-814
2. Nash R.J., Fellows L.E., Dring J.V., Stirton C.H., Carter D., Hegarty M.P., and Bell E.A. Phytochemistry 27 (1988) 1403-1404
3. Saul R., Chambers J.P., Molyneux R.J., and Elbein A.D. Arch. Biochem. Biophys. 227 (1983) 593-597
4. Pan Y.T., Hori H., Saul R., Sanford B.A., Molyneux R.J., and Elbein A.D. Biochemistry 22 (1983) 3975-3984
5. Dreyer D.L., Jones K.C., and Molyneux R.J. J. Chem. Ecol. 11 (1985) 1045-1051
6. Nash R.J., Evans S.V., Fellows L.E., and Bell E.A. In: Seawright A.A., Hegarty M.P., James L.F., and Keeler R.F. (Eds). Plant Toxicology (1985), Queensland Poisonous Plants Committee, Yeerongpilly, Australia 309
7. Trugnan G., Rousset M., and Zweibaum A. FEBS Lett. 795 (1986) 28-32
8. Fellows L.E. Pestic. Sci. 17 (1986) 602-606
9. Campbell B.C., Molyneux R.J., and Jones K.C. J. Chem. Ecol. 13 (1987) 1759-1770
10. Cenci di Bello I., Mann D., Nash R.J., and Winchester B.G. In: Salvayre R., Douste-Blazy L., and Gatt S. (Eds). Lipid Storage Disorders: Biological and Medical Aspects (1988), Plenum, New York, NY 635
11. Fellows L.E., and Fleet G.W.J. In: Wagman G.H., and Cooper R. (Eds). Natural Products Isolation (1989), Elsevier, New York, NY 539
12. Fellows L.E., Kite G., Nash R., Simmonds M., and Scofield A. In: Poulton J.E., Romeo J.T., and Conn E.E. (Eds). Plant Nitrogen Metabolism (1989), Plenum, New York, NY 395
13. Scofield A.M., Rossiter J.T., Witham P., Kite G.C., Nash R.J., and Fellows L.E. Phytochemistry 29 (1990) 107-109
14. Yamamoto I., Muto N., Murakami K., and Akiyama J. J. Nutr. 722 (1992) 871-877
15. Hempel A., Camerman N., Mastropaolo D., and Camerman A. J. Med. Chem. 36 (1993) 4082-4086
16. Valaitis A.P., and Bowers D.F. Insect Biochem. Mol. Biol. 23 (1993) 599-606
17. Walter S., Fassbender K., Gulbins E., Liu Y., Rieschel M., Herten M., Bertsch T., and Engelhardt B. J. Neuroimmunol. 132 (2002) 1-10
18. Schlesinger S., Koyama A.H., Malfer C., Gee S.L., and Schlesinger M.J. Virus Res. 2 (1985) 139-149
19. Sunkara P.S., Bowlin T.L., Liu P.S., and Sjoerdsma A. Biochem. Biophys. Res. Commun. 148 (1987) 206-210
20. Gruters R.A., Neefjes J.J., Tersmette M., De Goede R.E.Y., Tulp A., Huisman H.G., Miedema F., and Ploegh H.L. Nature 330 (1987) 74-77
21. Walker B.D., Kowalski M., Goh W.C., Kozarsky K., Krieger M., Rosen C., Rohrschneider L., Haseltine W.A., and Sodroski J. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 8120-8124
22. Tyms A.S., Berrie E.M., Ryder T.A., Nash R.J., Hegarty M.P., Taylor D.L., Mobberley M.A., David J.M., Bell E.A., Jeffries D.J., Taylor-Robinson D., and Fellows L.E. Lancet (1987) 1025-1026
23. Karpas A., Fleet G.W.J., Dwek R.A., Petursson S., Namgoog S.K., Ramsden N.G., Jacob G.S., and Rademacher T.W. Proc. Natl. Acad. Sci. U.S.A. 85 (1988) 9229-9233
24. Fleet G.W.J., Karpas A., Dwek R.A., Fellows L.E., Tyms A.S., Petursson S., Namgoong S.K., Ramsden N.G., Smith P.W., Son J.C., Wilson F., Witty D.R., Jacob G.S., and Rademacher T.W. FEBS Lett. 237 (1988) 128-132
25. Sunkara P.S., Taylor D.L., Kang M.S., Bowlin T.L., Liu P.S., Tyms A.S., and Sjoerdsma A. Lancet 333 (1989) 1206
26. Ruprecht R.M., Mullaney S., Anderson J., and Bronson R.J. J. Acquir. Immune Defic. Syndr. 2 (1989) 149-157
27. Bridges C.G., Brennan T.M., Taylor D.L., McPherson M., and Tyms A.S. Antiviral Res. 25 (1994) 169-175
28. Taylor D.L., Kang M.S., Brennan T.M., Bridges C.G., Sunkara P.S., and Tyms A.S. Antimicrob. Agents Chemother. 38 (1994) 1780-1787
29. Ahmed S.P., Nash R.J., Bridges C.G., Taylor D.L., Kang M.S., Porter E.A., and Tyms A.S. Biochem. Biophys. Res. Commun. 208 (1995) 267-273
30. Furneaux R.H., Gainsford G.J., Mason J.M., and Tyler P.C. Tetrahedron 53 (1997) 245-268
31. Ouzounov S., Mehta A., Dwek R.A., Block T.M., and Jordan R. Antiviral Res. 55 (2002) 425-435
32. Tyms, A. S. PCT Int. Appl. WO 2330336017, 2003;
33. Chem. Abstr. 138 (2003) 117633
34. Sasak V.W., Ordovas J.M., Elbein A.D., and Berninger R.W. Biochem. J. 232 (1985) 759-766
35. Trugnan G., Rousset M., and Zweibaum A. FEBS Lett. 195 (1986) 28-32
36. Humphries M.J., Matsumoto K., White S.L., and Olden K. Cancer Res. 46 (1986) 5215-5222
37. Dennis J.W. Cancer Res. 46 (1986) 5131-5136
38. Ahrens P.B., and Ankel H.J. J. Biol. Chem. 262 (1987) 7575-7579
39. Dennis J.W., Laferte S., Wahome C., Breitman M.L., and Kerbel R.S. Science 236 (1987) 582-585
40. Ostrander G.K., Scribner N.K., and Rohrschneider L.R. Cancer Res. 48 (1988) 1091-1094
41. Pili R., Chang J., Partis R.A., Mueller R.A., Chrest F.J., and Passaniti A. Cancer Res. 55 (1995) 2920-2926
42. Yee C.S., Schwab E.D., Lehr J.E., Quigley M., and Pienta K.J. Anticancer Res. 17 (1997) 3659-3663
43. Rhinehart B.L., Robinson K.M., Payne A.J., Wheatley M.E., Fisher J.L., Liu P.S., and Cheng W. Life Sci. 41 (1987) 2325-2331
44. Willenborg D.O., Parish C.R., and Cowden W.B. J. Neurol. Sci. 90 (1989) 77-85
45. Bartlett M.R., Cowden W.B., and Parish C.R. J. Leukocyte Biol. 57 (1995) 207-213
46. Grochowicz P.M., Hibberd A.D., Bowen K.M., Clark D.A., Pang G., Grochowicz L.K., Willenborg D.O., and Cowden W.B. Transplant. Proc. 27 (1995) 355-356
47. Hibberd A.D., Grochowicz P.M., Smart Y.C., Bowen K.M., Clark D.A., Purdon B., Willenborg D.O., and Cowden W.B. Transplant. Proc. 27 (1995) 448-449
48. Hibberd A.D., Grochowicz P.M., Smart Y.C., Bowen K.M., Clark D.A., Cowden W.B., and Willenborg D.O. Transplant. Proc. 29 (1997) 1257-1258
49. Grochowicz P.M., Hibberd A.D., Bowen K.M., Clark D.A., Pang G., Cowden W.B., Chou T.C., Grochowicz L.K., and Smart Y.C. Transplant. Proc. 29 (1997) 1259-1260
50. Whitby K., Pierson T.C., Geiss B., Lane K., Engel M., Zhou Y., Doms R.W., and Diamond M.S. J. Virol. 79 (2005) 8698-8706
51. For a review of published syntheses of 1 up to 1992 see:
52. Burgess B., and Henderson I. Tetrahedron 48 (1992) 4045-4066 For syntheses of 1 after 1992 see:
53. Ina H., and Kibayashi C. J. Org. Chem. 58 (1993) 52-61
54. Kim N.S., Choi J.R., and Cha J.K. J. Org. Chem. 58 (1993) 7096-7099
55. Grassberger V., Berger A., Dax K., Fechter M., Gradnig G., and Stuetz A.E. Liebigs Ann. Chem. (1993) 379-390
56. Zhao H., and Mootoo D.R. J. Org. Chem. 61 (1996) 6762-6763
57. Overkleeft H.S., and Pandit U.K. Tetrahedron Lett. 37 (1996) 547-550
58. Kang H., and Kim J.S. Chem. Commun. (1998) 1353-1354
59. Pandit U.K., Overkleeft H.S., Borer B.C., and Bieraugel H. Eur. J. Org. Chem. (1999) 959-968
60. Denmark S.E., and Martinborough E.A. J. Am. Chem. Soc. 121 (1999) 3046-3056
61. Zhao H., Hans S., Cheng X., and Mootoo D.R. J. Org. Chem. 66 (2001) 1761-1767
62. Somfai P., Marchand P., Torsell S., and Lindstrom U.M. Tetrahedron 59 (2003) 1293-1299
63. Zhao Z., Song L., and Mariano P.S. Tetrahedron 61 (2005) 8888-8894
64. Cronin L., and Murphy P.V. Org. Lett. 7 (2005) 2691-2693
65. Karanjule N.S., Markad S.D., Shind V.S., and Dhavale D.D. J. Org. Chem. 71 (2006) 4667-4670
66. Lindsay K.B., Tang M., and Pyne S.G. Synlett (2002) 731-734
67. Lindsay K.B., and Pyne S.G. J. Org. Chem. 67 (2002) 7774-7780
68. Tang M., and Pyne S.G. J. Org. Chem. 68 (2003) 7818-7824
69. Lindsay K.B., and Pyne S.G. Aust. J. Chem. 57 (2004) 669-672
70. Tang M., and Pyne S.G. Tetrahedron 60 (2004) 5759-5767
71. Pyne S.G., Davis A.S., Gates N.J., Hartley J.P., Lindsay K.B., Machan T., and Tang M. Synlett (2004) 2670-2680
72. Davis A.S., Pyne S.G., Skelton B.W., and White A.H. J. Org. Chem. 69 (2004) 3139-3143
73. Au C.W.G., and Pyne S.G. J. Org. Chem. 71 (2006) 7097-7099
74. Davis A.S., Gates N.J., Lindsay K.B., Tang M., and Pyne S.G. Synlett (2004) 49-52
75. Murray A.J., Parsons P.J., Greenwood E.S., and Viseux E.M.E. Synlett (2004) 1589-1591
76. Murray A.J., Parsons P.J., and Hitchcock P.B. Tetrahedron 63 (2007) 6485-6492
77. Byun H.-S., He L., and Bittman R. Tetrahedron 56 (2000) 7051-7091
78. An alternative mechanism for the formation of 13 from the cyclization of 11 (Scheme 2), may involve terminal alkoxide displacement of the carboxylate moiety of the cyclic carbamate. This would produce 2-epi-13. The fact that the same compound 13 is produced in both Schemes 2 and 3 suggests that this alternative mechanism does not occur since the primary hydroxyl in 12 would be expected to be selectively activated under Mitsunobu cyclization conditions. We thank a referee for bringing this to our attention.
79. Mulzer J., and Dehmlow H. J. Org. Chem. 57 (1992) 3194-3202
80. Casiraghi G., Ulgheri F., Spanu P., Rassu G., Pinna L., Gasparri F.G., Belicchi F.M., and Pelosi G. J. Chem. Soc., Perkin Trans. 1 (1993) 2991-2997
81. Naruse M., Aoyagi S., and Kibayashi C. J. Org. Chem. 59 (1994) 1358-1364
82. Chen Y., and Vogel P. J. Org. Chem. 59 (1994) 2487-2496
83. see Ref. 10j;
84. Zhou W.-S., Xie W.-G., Lu Z.-H., and Pan X.-F. Tetrahedron Lett. 36 (1995) 1291-1294
85. Kindly supplied by Dr. Reg Smith Phytex, Sydney.