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{ H",o V B: --' 35 36 1clyO XV • 39 / o 37 38 \ .0 0 30 OH OH
The HRMS of 41 exhibits a base peak at m / z 123 (CaH lIQ) which can be attributed to formation of fragment A via the mechanism shown below o This data suggests that compound 41 has structure 39; consequently anhydroarthrosporone (21) has structure 35. The lH NMR spectrum of compound 41 gives further support to the structural assignment. A low field proton (0 5.95, q. J = 1.6 Hz) shows allylic coupling to a methyl group (0 2.05. d, J = 1.6 Hz). Three methyl singlets (0 1.45, 1.19 and 1.04) and a methyl doublet (0 1.08, J = 7.5 Hz), which is coupled to a methine proton (0 2.08, q), are observed. These data are consistent with the partial structure XVI. The remainder of the spectrum shows a set of proton multiplets (Scheme VIII). A similar spin system consistent with partial structure XVII has precedence in the literature U in the structure of Fomannosin (42) and its derivative 43. The long range coupling (cJ = 2.5 Hz) observed in anhydroarthrosporone has also been observed in 43 and cybrodol (44).Cl • A o 31
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 21 and 22: 18 OH anhydroarthrosporone 12 11. a
Page 24 and 25: major components as evidenced by ex
Page 26: The IH-NMR spectrum of arthrosporon
Page 31 and 32: (C) 1 1 CH) o OH ml z 252 IM-) CH)
Page 33 and 34: 28 HO OH 30 32 OH OH o o o 29 33 31
Page 35: (C) o Àmax (calcdl 231 nm; obs. 23
Page 39: expected to undergo a retro-aldol c
Page 49 and 50: molecular formula was established a
Page 55 and 56: downfield proton (H-4) at 0 3.84. T
Page 57 and 58: Examination of the IH NMR spectra o
Page 59 and 60: Figure 6: Ring C viewed from the to
Page 62: Table 9: lH NMR Spectral Data for A
Page 65 and 66: 21 Scheme XIII in which the reactio
Page 67 and 68: HO HO OH 9 21 &0 " OH 0 60 Scheme X
Page 69 and 70: fully substituted carbons bearing o
Page 71 and 72: 83= 20 o AI R -= Ac 12 R-=H _-OH Ta
Page 73: Table 13. IR Spectral Data (CHCI] c
Page 76 and 77: 47 .....OH The IH NMR data for 68 s
Page 79: The striking difference between the
Page 83 and 84: Table 18. IH NMR Spectral Data for
Page 85: The IH NMR spectrum of 23 (Figure 1
Page 88: The IH NMR spectrum of 24 (Figure 1
Page 92 and 93:
Further evidence for the configurat
Page 97 and 98:
(Cl XXIV H H XXII H H H XXIII H HO
Page 99:
Table 20. lH NMR Spectra Data for I
Page 103 and 104:
spectrometer coupled to a D5-9 comp
Page 105 and 106:
Separation of the Neutral Metabolit
Page 107 and 108:
An impure fraction (1 10 mg) contai
Page 109:
H-9b), 1.97 (1H, brt, 12 Hz, H-1 1a
Page 118:
The unsaturated acetate 34 (5 mg, 0
Page 122 and 123:
cm- I . HREIMS: mlz (formula. inten
Page 124:
FTIR (CHCl l , cast): 3424 (br), 29
Page 128 and 129:
(ether / Skellysolve BI keta-dial 6
Page 130 and 131:
Hz), 1.48 (2H, M), 1.09 (3H, s), 1.
Page 132 and 133:
FTIR: (CHCI!, 0.1 MM) 3560. 1716 (s
Page 134 and 135:
cis-2{3-3a, 10, 10-Tetramethyltricy
Page 137 and 138:
13.5 and 4 Hz, H-6b), 2.34 (1H, td,
Page 139 and 140:
Table 4: Antibiotic Bioassay of Cru
Page 141 and 142:
Table 6: Antifungal Bioassay of Pur
Page 143 and 144:
BIBLIOGRAPHY 1. Hiratsuka. Y.; Tsun
Page 145 and 146:
2720. 25. Turner, W.B,; Aldridge, D
Page 147 and 148:
. Dauben, W.G.; Hart, D.J. J. Org.
Page 149:
69. a. Hashimoto, H.; Ito, T., Mats
Page 153 and 154:
6 5 4 3 2 Figure 3. 400 MHz IH NMR
Page 155:
imp. J'---J.------I • , t t ! 1 4
Page 158:
,---r 1 1 ! , 1 ! l , 3 ( 1 ! 1 ! 2
Page 162 and 163:
Entrée 1 - Préambule 2 - Abstract
Page 165:
INTRODUCTION Dans le cadre de la re
Page 172:
1) un carbonyle appartenant à un s
Page 177:
V Préparation des dérivés 1 - 8-
Page 180 and 181:
13 - OXYDATION DE LA DEHYDROARTHROS
Page 182 and 183:
BIBLIOGRAPHIE 1. R. J. Stipes and R
Page 184:
HC 3 C02 Et 0 C0 2 Et H 3 C H 3 C H
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