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Scheme 5.2 Synthesis toward lichostatinal (5.4). ................................................................. 255 Scheme 5.3 Ito’s reduction of Cbz protected arginine 5.22. ................................................. 257 Scheme 5.4 Oxidation of Arginol (5.24). ............................................................................. 258 Scheme 5.5 Synthesis towards lichostatinal (5.4). ................................................................ 259 Scheme 5.6 Alternative route to lichostatinal (5.4). ............................................................. 261 Scheme 6.1 Syntheses towards polar analogues of 4.4. ........................................................ 304 Scheme 6.2 Lithiation strategy to construct A-ring analogues of 4.4. .................................. 305 Scheme 6.3 Deprotection of regiosisomer 4.24. ................................................................... 306 Scheme 6.4 Alternative synthesis of regioisomer (±)-6.9. .................................................... 307 xxii
List of Symbols and Abbreviations �� - degree(s) % - percent (�) - racemic AcOH - acetic acid AF1 - activation function 1 AIBN - azobisisobutyronitrile AKT - protein kinase B Ala - alanine AR - androgen receptor Asp - aspartic acid br - broad Bn - benzyl Boc - t-butoxycarbonyl BRSM - based on recovered starting material Bu - butyl n-BuLi - n-butyllithium t-BuLi - t-butyllithium �C - degrees Celsius 15C-5 - 1,4,7,10,13-pentaoxacyclopentadecane 18C-6 - 1,4,7,10,13,16-hexaoxacyclooctadecane CA - California calcd - calculated Cbz - carboxybenzyl CDI - carbonyldiimidazole CLogP - calculated octanol/water partition coefficient COSY - two-dimensional correlation spectroscopy CRPC - castrate recurrent prostate cancer Cyp - cyproheptadine Cys - cysteine � - chemical shift in parts per million d - doublet DBU - 1,8-diazabicyclo[5.4.0]undec-7-ene DCM - dichloromethane dd - doublet of doublets DHEA - dehydroepiandrosterone DIBAL-H - diisobutylaluminium hydride DIEA - N,N-diisopropylethylamine DIPT - diisopropyl tartrate DMAP - 4-dimethylaminopyridine DMF - N,N-dimethylformamide DMP - Dess–Martin periodinane DMS - dimethyl sulfide DMSO - dimethyl sulfoxide DNA - deoxyribonucleic acid xxiii
Page 1 and 2: FUNCTION ORIENTED SYNTHESIS OF BIOA
Page 3 and 4: The fifth chapter describes synthet
Page 5 and 6: iological data and “click” chem
Page 7 and 8: 2.6 Synthesis of a Benzophenone Pho
Page 9 and 10: List of Tables Table 1.1 The proper
Page 11 and 12: Figure 2.12 CLogP values of 2.18 an
Page 13 and 14: Figure 2.41 1 H and 13 C NMR spectr
Page 17 and 18: Figure 4.6 AR competitor in vitro a
Page 21: Scheme 3.5 Synthesis of (R)-niphate
Page 25 and 26: Lys - lysine m - multiplet M - mola
Page 27 and 28: Acknowledgements What a trip. First
Page 29 and 30: Chapter 1: Marine Natural Products
Page 31 and 32: Table 1.1 The properties of natural
Page 33 and 34: deprotonates the secondary alcohol
Page 35 and 36: Figure 1.4 Marine natural product i
Page 37 and 38: sceptrin 28 (1.20), and (-)-agelife
Page 39 and 40: polyketide (+)-spongistatin 1 (1.27
Page 41 and 42: allowing for construction of simpli
Page 43 and 44: potency, and the synthetic efforts
Page 45 and 46: 4,5-P2, or PIP2). This generates an
Page 47 and 48: Figure 2.3 Pelorol (2.1) analogue 2
Page 49 and 50: 2.3 Synthesis of SHIP1 Activators U
Page 51 and 52: intramolecular attack by a nucleoph
Page 53 and 54: Scheme 2.4 Elimination side product
Page 55 and 56: As this issue of water solubility i
Page 57 and 58: Scheme 2.5 Inspiration for biomimet
Page 59 and 60: Scheme 2.7 Synthesis of amine analo
Page 61 and 62: Figure 2.13 ORTEP diagram of Mosher
Page 63 and 64: Reductive amination of oxime 2.41 g
Page 65 and 66: While primary amines 2.20 and 2.42
Page 67 and 68: interacts with SHIP1 and if there i
Page 69 and 70: Figure 2.18 STDD NMR sample prepara
Page 71 and 72: STDD effects are observed for proto
Page 73 and 74:
Figure 2.22 Commonly used tags. The
Page 75 and 76:
enzophenone fragment can come from
Page 77 and 78:
with thionyl chloride gave acid chl
Page 79 and 80:
These two regioisomers could not be
Page 81 and 82:
This sample was stirred at room tem
Page 83 and 84:
minor �-amine epimers 2.34/2.43 s
Page 85 and 86:
2.8 Conclusion The activation of SH
Page 87 and 88:
mouse model. The compounds were eff
Page 89 and 90:
otations were measured with a JASCO
Page 91 and 92:
Preparation of 2.3/2.14: To a solut
Page 93 and 94:
Figure 2.28 1 H and 13 C NMR spectr
Page 95 and 96:
Preparation of (±)-2.26: To polyen
Page 97 and 98:
Preparation of 2.30: To epoxide 2.2
Page 99 and 100:
Preparation of 2.31: Alcohol 2.30 (
Page 101 and 102:
Page 103 and 104:
Page 105 and 106:
Page 107 and 108:
Page 109 and 110:
Compound 2.20: 1 H NMR (600 MHz, CD
Page 111 and 112:
Page 113 and 114:
Preparation of 2.40: To 2.19 (20 mg
Page 115 and 116:
Preparation of 2.44: To 2.40 (10.3
Page 117 and 118:
Preparation of 2.45: To 2.44 (8.0 m
Page 119 and 120:
Preparation of 2.47: To sodium hydr
Page 121 and 122:
Preparation of 2.61: To acid chlori
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Preparation of 2.53: To 2.61 (754 m
Page 125 and 126:
Figure 2.42 NOESY spectrum of 2.53
Page 127 and 128:
Dry Transfer system (Life Technolog
Page 129 and 130:
Chapter 3: Glycerol Ethers from the
Page 131 and 132:
Figure 3.2 Examples of antiandrogen
Page 133 and 134:
Figure 3.4 Small molecule antagonis
Page 135 and 136:
the benzyl protected glycerol ether
Page 137 and 138:
The synthesis of (R)-niphatenone B
Page 139 and 140:
and B (3.37) were isolated by Matsu
Page 141 and 142:
Scheme 3.8 Synthesis of a short cha
Page 143 and 144:
(3.31). This was accomplished by op
Page 145 and 146:
Acetonide 3.30 was hydrogenated in
Page 147 and 148:
of an active probe is the quinoline
Page 149 and 150:
conjugation is disrupted by the nuc
Page 151 and 152:
Figure 3.11 AR transcriptional acti
Page 153 and 154:
concentration of either (S) or (R)
Page 155 and 156:
Each natural product contains one s
Page 157 and 158:
Preparation of 3.16: Tetrahydrofura
Page 159 and 160:
Preparation of 3.17: To compound 3.
Page 161 and 162:
Preparation of 3.18: To alcohol 3.1
Page 163 and 164:
Preparation of 3.20: Phosphorane 3.
Page 165 and 166:
Page 167 and 168:
Page 169 and 170:
Preparation of 3.27: NaH (330 mg, 8
Page 171 and 172:
Page 173 and 174:
Preparation of 3.29: To Dess-Martin
Page 175 and 176:
Preparation of 3.30: To phosphonate
Page 177 and 178:
Preparation of 3.31: To acetonide 3
Page 179 and 180:
Preparation of 3.35: Procedures ide
Page 181 and 182:
Preparation of 3.34: To bromohydrin
Page 183 and 184:
Preparation of 3.25: To bromide 3.3
Page 185 and 186:
Page 187 and 188:
Page 189 and 190:
Preparation of 3.41: To ketone 3.40
Page 191 and 192:
Page 193 and 194:
Page 195 and 196:
Page 197 and 198:
Page 199 and 200:
Preparation of 3.48: Sodium hydride
Page 201 and 202:
Page 203 and 204:
Preparation of 3.50: To Dess-Martin
Page 205 and 206:
Page 207 and 208:
Page 209 and 210:
Page 211 and 212:
Page 213 and 214:
Preparation of 3.57: To bromine 3.2
Page 215 and 216:
Preparation of 3.58:� To 3.57 (2.
Page 217 and 218:
Preparation of 3.59:� To alcohol
Page 219 and 220:
Page 221 and 222:
Page 223 and 224:
Page 225 and 226:
Page 227 and 228:
Page 229 and 230:
AR Transcriptional Activity Assay:
Page 231 and 232:
Chapter 4: Synthetic Efforts Toward
Page 233 and 234:
Scheme 4.1 Semisynthesis of 4.1 ana
Page 235 and 236:
This synthetic route was devised wi
Page 237 and 238:
Scheme 4.5 Synthesis of regioisomer
Page 239 and 240:
Figure 4.4 Favored and disfavored r
Page 241 and 242:
An alternative strategy using 3-fur
Page 243 and 244:
Scheme 4.10 Mono-thiolated analogue
Page 245 and 246:
4.4 Biological Results The semisynt
Page 247 and 248:
Table 4.1 EC50 values for tested co
Page 249 and 250:
The focus of this chapter is dedica
Page 251 and 252:
Preparation of 4.16: To a solution
Page 253 and 254:
Page 255 and 256:
Page 257 and 258:
Preparation of 4.20: To (-)-DIPT (0
Page 259 and 260:
Page 261 and 262:
Preparation of 4.22: To bromide 4.1
Page 263 and 264:
Preparation of 4.23: To sulfone 4.2
Page 265 and 266:
Page 267 and 268:
Preparation of 4.40: To furan 4.12
Page 269 and 270:
Page 271 and 272:
Page 273 and 274:
Page 275 and 276:
Page 277 and 278:
Chapter 5: Synthetic Efforts Toward
Page 279 and 280:
Shortly afterwards, additional pept
Page 281 and 282:
the nM range in a cathepsin K enzym
Page 283 and 284:
Scheme 5.2 Synthesis toward lichost
Page 285 and 286:
primary alcohol and oxidizing it ba
Page 287 and 288:
was attempted in order to shorten f
Page 289 and 290:
Scheme 5.6 Alternative route to lic
Page 291 and 292:
ligand complex was analyzed by a be
Page 293 and 294:
Preparation of 5.12: To Fmoc-L-vali
Page 295 and 296:
Preparation of 5.13: To 5.12 (7.0 g
Page 297 and 298:
Preparation of 5.15: To O-benzyl-Bo
Page 299 and 300:
Page 301 and 302:
Preparation of 5.18: Mono Boc prote
Page 303 and 304:
Figure 5.9 1 H and 13 C NMR spectra
Page 305 and 306:
127.5, 127.4, 72.2, 70.6, 63.1, 57.
Page 307 and 308:
Page 309 and 310:
Page 311 and 312:
Page 313 and 314:
Preparation of 5.32: To Fmoc-L-seri
Page 315 and 316:
Preparation of 5.33: 5.32 (591.3 mg
Page 317 and 318:
Preparation of 5.35: To the Fmoc pr
Page 319 and 320:
Preparation of 5.36: Compound 5.35
Page 321 and 322:
Page 323 and 324:
Page 325 and 326:
Preparation of 5.39: To Boc protect
Page 327 and 328:
Page 329 and 330:
Chapter 6: Conclusion 6.1 Biologica
Page 331 and 332:
either niphatenone A (3.8) and/or B
Page 333 and 334:
Scheme 6.2 Lithiation strategy to c
Page 335 and 336:
Scheme 6.4 Alternative synthesis of
Page 337 and 338:
References (1) McGovern, P. E.; Mir
Page 339 and 340:
(31) Seiple, I. B.; Su, S.; Young,
Page 341 and 342:
(55) Woodward, R.; Bloch, K. J. Am.
Page 343 and 344:
(86) Parra-Delgado, H.; Compadre, C
Page 345 and 346:
(112) Bi, X.; Schmitz, A.; Hayallah
Page 347 and 348:
(140) Sadar, M. D.; Williams, D. E.
Page 349 and 350:
(167) Zoretic, P.; Wang, M.; Zhang,
Page 351 and 352:
(199) Mohamed, M. M.; Sloane, B. F.
Page 353 and 354:
(224) Shimokawa, J.; Ishiwata, T.;
Page 355 and 356:
Crystal Data: Empirical Formula C23
Page 357 and 358:
Structure Solution and Refinement:
Page 359 and 360:
Crystal Data: Empirical Formula C33
Page 361 and 362:
Page 363 and 364:
non-hydrogen atoms were refined ani
Page 365:
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