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H0 2 C H0 2 C Schema 1. In Vitro Transformation of Hlrsutlc Acld 14 12 LiBH•. THF OH OH OH MnO J • CHCI) .. H0 2 MnO J • CHCI) , C' , , H0 2 C 13 15 OH o ° tD
Page 1: THE UI\JIVERSITY OF ALBERTA ANTIFUN
Page 4 and 5: Abstract A fungus observed to inhib
Page 6 and 7: Acknowledgements 1would like to exp
Page 8 and 9: LIST Of TABLES Table Page 1. Taxono
Page 10 and 11: LIST OF SCHEMES Scheme Page 1. ln v
Page 12: of the landscape. C. ulmi. causal a
Page 15 and 16: Fig. 1. Photo of Arthrosporae fungu
Page 17: 8 9 10 11 7 OH RI =O. Rl =
Page 22: the triol 22. Its structure was con
Page 25 and 26: acetate 1pentane 1: 1L* A reddish c
Page 28: H appears as a doublet (J = 14Hz) a
Page 32 and 33: in 20 (0 2.56 (ddl. 2.40 (dl and 0
Page 34 and 35: visualized on analytical tic using
Page 37: The spectroscopie data led to the f
Page 40 and 41: { H",o V B: --' 35 36 1clyO XV •
Page 43: Bond formation between C-' (partial
Page 50: Table 5: IH NMR Spectral Data for A
Page 56 and 57: 50 28 = 20 OH 51 ......OH o KOHl Et
Page 58 and 59: Table 7. lH NMR Spectral Data for A
Page 60: which the C-3 methyl is in the a co
Page 64 and 65: 58 DAc o o o 61.25 1 1 61.15 Table
Page 66 and 67: The IH NMR spectrum of 60 shows a s
Page 68 and 69:
more complex reaction occurred. Inv
Page 70 and 71:
arthrosporone (20) was subjected to
Page 72 and 73:
oil. Monoacetate 66 is the most pol
Page 75 and 76:
Table 15. lH NMR Spectral Data for
Page 77:
Reduction of arthrosporone al 50 pr
Page 82 and 83:
Conclusive evidence that Î soarthr
Page 84 and 85:
o A À max (calcd.) = 239 nm c B (e
Page 87 and 88:
OH, 1696, 1616 cm-I). The lH NMR sp
Page 90:
oxygen atom. This coupling pattern
Page 93:
Table 19. Chemical Shift for H·" i
Page 98 and 99:
as that of H-6a. H-6tl (0 2.79) and
Page 102 and 103:
III. EXPERIMENTAL Distilled water u
Page 104 and 105:
weeks. The shake culture (400 mU wa
Page 106 and 107:
Table 1. POlarity of the Gradient E
Page 108 and 109:
Purification of eis,anti,eis-2{3,3{
Page 115:
1.60 (lH, t, 12 Hz, H-lla), 1.51 (l
Page 121 and 122:
FTIR (CH,CI 2, cast): 3502 (strong)
Page 123 and 124:
(C 4H 9 ,41.8). IH NMR (CDCI 3 ): 0
Page 126:
15.0 Hz, H-9b), 1.06 (3H, s, H-13),
Page 129 and 130:
HREIMS: ml z (fragment, intensity),
Page 131 and 132:
(Skellysolve B / diethyl ether): m.
Page 133 and 134:
CIMS (NHJ mlz calcd for M+ 18: 398;
Page 135:
DMAP were added and the mixture was
Page 138 and 139:
Table 3. Antibiotic Bioassay of Cru
Page 140 and 141:
Table 5: Antifungal Bioassay of Cru
Page 142 and 143:
Table 7: Antifungsl Bioassay of Kno
Page 144 and 145:
. 24. a. b. Bennett, JW.; Ciegler,
Page 146 and 147:
35. a. b. c. 37. a. b. 38. a. b. 39
Page 148 and 149:
55. a. Poppleston, C.R. Cano J. Che
Page 151:
APPENDIX 141
Page 154 and 155:
4 3 2 FIgure 7. 400 MHz lH NMR spec
Page 157 and 158:
Figure 13. 400 MHz IH NMR spectrum
Page 161 and 162:
SESQUITERPENOïDES ANTIFONGIQUES D'
Page 163:
Cette thèse a été soumise à la
Page 170:
· Quant à ce qui concerne l'arthr
Page 174:
\1 Culture du Champignon Arthrospor
Page 179 and 180:
9 - 4-0-ACETYLARTHROSPOROL 16 Une s
Page 181 and 182:
CONCLUSION Les études entreprises
Page 183 and 184:
H 3 C H 3 C 1 R'=R"=H 5 R'=Ac R"=H
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