A Route to Carbasugar Analogues - Jonathan Clayden - The ...

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H8 H 0.9757 -0.1848 0.2244 0.024 Uiso 1 1 calc R . . C9 C 0.9635(9) -0.0603(6) 0.1125(5) 0.0229(17) Uani 1 1 d . . . H9 H 1.0853 -0.0579 0.1025 0.027 Uiso 1 1 calc R . . C10 C 0.9453(9) 0.0119(7) -0.0695(5) 0.0279(18) Uani 1 1 d . . . H10A H 1.0618 0.0393 -0.0712 0.042 Uiso 1 1 calc R . . H10B H 0.8791 0.0645 -0.1168 0.042 Uiso 1 1 calc R . . H10C H 0.9525 -0.0739 -0.0920 0.042 Uiso 1 1 calc R . . C11 C 0.5454(9) 0.0443(6) -0.0236(5) 0.0223(17) Uani 1 1 d . . . H11 H 0.6190 0.0828 -0.0822 0.027 Uiso 1 1 calc R . . C12 C 0.4243(9) 0.1496(6) 0.0289(5) 0.0264(18) Uani 1 1 d . . . H12A H 0.3248 0.1149 0.0686 0.040 Uiso 1 1 calc R . . H12B H 0.3842 0.2073 -0.0251 0.040 Uiso 1 1 calc R . . H12C H 0.4870 0.1934 0.0765 0.040 Uiso 1 1 calc R . . C13 C 0.4397(9) -0.0432(7) -0.0725(5) 0.0259(18) Uani 1 1 d . . . H13A H 0.5167 -0.1032 -0.1143 0.039 Uiso 1 1 calc R . . H13B H 0.3629 0.0033 -0.1178 0.039 Uiso 1 1 calc R . . H13C H 0.3707 -0.0868 -0.0173 0.039 Uiso 1 1 calc R . . C14 C 0.8597(9) 0.4533(6) -0.0172(5) 0.0249(17) Uani 1 1 d . . . C15 C 0.7715(9) 0.5669(6) -0.0271(5) 0.0305(19) Uani 1 1 d . . . H15 H 0.6688 0.5886 0.0173 0.037 Uiso 1 1 calc R . . C16 C 0.8362(11) 0.6506(7) -0.1041(6) 0.042(2) Uani 1 1 d . . . H16 H 0.7752 0.7291 -0.1119 0.051 Uiso 1 1 calc R . . C17 C 0.9843(11) 0.6218(7) -0.1680(6) 0.042(2) Uani 1 1 d . . . H17 H 1.0246 0.6798 -0.2198 0.051 Uiso 1 1 calc R . . C18 C 1.0751(11) 0.5093(7) -0.1576(6) 0.046(2) Uani 1 1 d . . . H18 H 1.1790 0.4889 -0.2012 0.055 Uiso 1 1 calc R . . C19 C 1.0103(10) 0.4241(7) -0.0804(5) 0.035(2) Uani 1 1 d . . . H19 H 1.0717 0.3459 -0.0722 0.042 Uiso 1 1 calc R . . C20 C 0.8762(8) 0.3833(6) 0.2535(5) 0.0191(16) Uani 1 1 d . . . C21 C 0.9035(8) 0.5081(6) 0.2635(5) 0.0257(18) Uani 1 1 d . . . H21 H 0.9387 0.5557 0.2029 0.031 Uiso 1 1 calc R . . C22 C 0.8799(9) 0.5617(6) 0.3595(5) 0.0262(18) Uani 1 1 d . . . H22 H 0.8978 0.6465 0.3647 0.031 Uiso 1 1 calc R . . C23 C 0.8302(9) 0.4941(7) 0.4495(6) 0.0283(19) Uani 1 1 d . . . H23 H 0.8204 0.5310 0.5163 0.034 Uiso 1 1 calc R . . C24 C 0.7947(9) 0.3712(6) 0.4406(5) 0.0270(18) Uani 1 1 d . . . H24 H 0.7539 0.3250 0.5008 0.032 Uiso 1 1 calc R . . C25 C 0.8199(8) 0.3175(6) 0.3424(5) 0.0234(17) Uani 1 1 d . . . 311
H25 H 0.7979 0.2335 0.3365 0.028 Uiso 1 1 calc R . . C26 C 0.2928(9) 0.7886(6) 0.5233(5) 0.0224(17) Uani 1 1 d . . . C27 C 0.2850(9) 0.5816(6) 0.5312(5) 0.0236(17) Uani 1 1 d . . . H27 H 0.1826 0.5452 0.5079 0.028 Uiso 1 1 calc R . . C28 C 0.4031(9) 0.6214(6) 0.4357(5) 0.0210(17) Uani 1 1 d . . . H28 H 0.5243 0.5916 0.4473 0.025 Uiso 1 1 calc R . . C29 C 0.2556(8) 0.9190(6) 0.5639(5) 0.0180(16) Uani 1 1 d . . . C30 C 0.0682(8) 0.9745(6) 0.5535(5) 0.0140(14) Uani 1 1 d . . . H30 H 0.0647 1.0600 0.5807 0.017 Uiso 1 1 calc R . . C31 C 0.0448(9) 0.9934(6) 0.4366(5) 0.0225(17) Uani 1 1 d . . . H31 H 0.0790 0.9140 0.3996 0.027 Uiso 1 1 calc R . . C32 C 0.1555(9) 1.0903(6) 0.3893(5) 0.0225(17) Uani 1 1 d . . . H32 H 0.1010 1.1732 0.4115 0.027 Uiso 1 1 calc R . . C33 C 0.3330(9) 1.0742(6) 0.4230(5) 0.0201(16) Uani 1 1 d . . . H33 H 0.4182 1.1217 0.3870 0.024 Uiso 1 1 calc R . . C34 C 0.3810(8) 0.9986(6) 0.4995(5) 0.0198(16) Uani 1 1 d . . . H34 H 0.4976 0.9939 0.5147 0.024 Uiso 1 1 calc R . . C35 C 0.2973(9) 0.9194(6) 0.6791(5) 0.0254(18) Uani 1 1 d . . . H35A H 0.2327 0.8579 0.7203 0.038 Uiso 1 1 calc R . . H35B H 0.2642 1.0014 0.7081 0.038 Uiso 1 1 calc R . . H35C H 0.4213 0.8992 0.6818 0.038 Uiso 1 1 calc R . . C36 C -0.0775(8) 0.9141(6) 0.6224(5) 0.0227(17) Uani 1 1 d . . . H36 H -0.0242 0.8779 0.6851 0.027 Uiso 1 1 calc R . . C37 C -0.1550(9) 0.8070(6) 0.5732(6) 0.0305(19) Uani 1 1 d . . . H37A H -0.2353 0.8402 0.5238 0.046 Uiso 1 1 calc R . . H37B H -0.2169 0.7587 0.6285 0.046 Uiso 1 1 calc R . . H37C H -0.0622 0.7539 0.5360 0.046 Uiso 1 1 calc R . . C38 C -0.2183(8) 1.0112(6) 0.6644(5) 0.0266(18) Uani 1 1 d . . . H38A H -0.1674 1.0721 0.7038 0.040 Uiso 1 1 calc R . . H38B H -0.3062 0.9713 0.7106 0.040 Uiso 1 1 calc R . . H38C H -0.2716 1.0526 0.6056 0.040 Uiso 1 1 calc R . . C39 C 0.3716(9) 0.4925(6) 0.6067(5) 0.0237(18) Uani 1 1 d . . . C40 C 0.4876(9) 0.5309(7) 0.6681(5) 0.0303(19) Uani 1 1 d . . . H40 H 0.5105 0.6154 0.6660 0.036 Uiso 1 1 calc R . . C41 C 0.5743(10) 0.4474(8) 0.7348(6) 0.043(2) Uani 1 1 d . . . H41 H 0.6574 0.4743 0.7761 0.052 Uiso 1 1 calc R . . C42 C 0.5353(12) 0.3248(8) 0.7387(7) 0.053(3) Uani 1 1 d . . . H42 H 0.5905 0.2676 0.7842 0.064 Uiso 1 1 calc R . . 312
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Dearomatising Addition of Organolit
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2.3 Synthetic Scope 64 2.3.1 Organo
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Abstract Dearomatising Addition of
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The Author The Author graduated fro
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Abbreviations & Conventions Ac acet
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RDS rate determining step R f RC rt
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Chapter 1: Introduction Chapter 1 -
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Chapter 1: Introduction controlled
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Chapter 1: Introduction diastereome
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Chapter 1: Introduction combine mor
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Chapter 1: Introduction O Ar Cl TMP
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Chapter 1: Introduction conditions,
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Chapter 1: Introduction chiral oxaz
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Chapter 1: Introduction Again a lar
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Chapter 1: Introduction 34 Scheme 1
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Chapter 1: Introduction The amino a
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Chapter 1: Introduction It was envi
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Chapter 1: Introduction COR' i) ATP
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Chapter 1: Introduction O i) ATPH,
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Chapter 1: Introduction 1.4 Nucleop
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Chapter 1: Introduction Unlike the
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Chapter 1: Introduction Diene (-)-8
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Chapter 1: Introduction A scheme su
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Chapter 1: Introduction Cl R + 93 S
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Chapter 2 - Dearomatising additions
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3.1 - Oxazoline synthesis 3.1.1.a H
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3.1 - Oxazoline synthesis O Ar OH i
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3.1 - Oxazoline synthesis 3.1.2 Gen
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3.1 - Oxazoline synthesis mCPBA O N
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3.1 - Oxazoline synthesis 3.1.4.b M
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3.1 - Oxazoline synthesis Ph Ph Ph
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3.2 - Oxazoline removal O N O OH 3N
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3.2 - Oxazoline removal O Me O N OM
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3.2 - Oxazoline removal However, th
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3.2 - Oxazoline removal 3.2.3 Reduc
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3.2 - Oxazoline removal Ph O N Ph P
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3.2 - Oxazoline removal 3.2.3.c Ami
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3.2 - Oxazoline removal Ph Ph Ph Ph
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3.2 - Oxazoline removal 3.2.5.b N-A
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3.2 - Oxazoline removal Ph Ph O N H
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3.2 - Oxazoline removal Ph Me Ph Me
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3.2 - Oxazoline removal 3.2.6 Deter
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Better, however, would be a method
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4.1 - Introduction HO OH OH HO OH O
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4.1 - Introduction (-)-Shikimic aci
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4.1 - Introduction followed by Flem
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4.2 - Carbasugar synthesis 4.2 Synt
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4.2 - Carbasugar synthesis stereoce
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4.2 - Carbasugar synthesis of the o
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4.2 - Carbasugar synthesis support
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4.2 - Carbasugar synthesis Ox* Ox*
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4.2 - Carbasugar synthesis OsO 4 (c
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4.2 - Carbasugar synthesis taken on
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4.2 - Carbasugar synthesis As well
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4.4 - Revised altrose synthesis 4.4
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4.4 - Revised altrose synthesis suf
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4.4 - Revised altrose synthesis ind
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4.5 - Mannose synthesis 4.5 Synthes
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4.5 - Mannose synthesis It is clear
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4.5 - Mannose synthesis considering
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4.5 - Mannose synthesis which would
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4.5 - Mannose synthesis One clear a
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4.5 - Mannose synthesis 4.5.2.b Epo
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4.5 - Mannose synthesis hydrolysis
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4.5 - Mannose synthesis The second
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4.6 - Summary 4.6 Summary & Future
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4.6 - Summary OH CDI, NH 2 OH.HCl,
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184
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References (37) Rawson, D. J.; Meye
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References (105) Gajewski, J. J.; B
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References (169) McCormick, J. P.;
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References 192
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Experimental section 254nm, dodecam
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Experimental section General Proced
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Experimental for chapter 2 Synthesi
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Experimental for chapter 2 (CDCl 3
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Experimental for chapter 2 3H, OMe
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Experimental for chapter 2 Ph), 139
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Experimental for chapter 2 H4), 5.2
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Experimental for chapter 2 108 R f
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Experimental for chapter 2 Synthesi
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Experimental for chapter 3.1 satura
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Experimental for chapter 3.1 Na 2 S
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Experimental for chapter 3.1 Synthe
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Experimental for chapter 3.1 128.9,
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Experimental for chapter 3.1 Microw
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Experimental for chapter 3.1 R f :
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Experimental for chapter 4.1 281 R
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Experimental for chapter 4.1 combin
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Experimental for chapter 4.1 291 R
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Experimental for chapter 4.1 3H, OB
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Page 263 and 264: Experimental for chapter 4.2 (1S*,2
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Page 267 and 268: Experimental for chapter 4.2 10.0,
Page 269 and 270: Experimental for chapter 4.2 cm 3 )
Page 271 and 272: Experimental for chapter 4.2 Synthe
Page 273 and 274: Experimental for chapter 4.2 5.7 Re
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Page 285 and 286: Absolute structure parameter 1.3(11
Page 287 and 288: _diffrn_standards_interval_time ? _
Page 289 and 290: H13 H 0.8405 0.7136 -0.0889 0.026 U
Page 291 and 292: C4 C5 1.454(2) . ? C5 C6 1.324(2) .
Page 293 and 294: C24 C23 C22 120.0(2) . . ? C24 C23
Page 295 and 296: . Compound 102c Ph O N Ph Me 102c O
Page 297 and 298: _diffrn_standards_interval_time ? _
Page 299 and 300: H11 H 0.8924 0.9592 0.6829 0.022 Ui
Page 301 and 302: C2 H2 1.0000 . ? C3 C21 1.506(2) .
Page 303 and 304: C26 C21 C3 121.41(15) . . ? C23 C22
Page 305 and 306: c. Compound 213 Ph O N Ph Me OH 213
Page 307 and 308: _cell_volume 1080.9(4) _cell_formul
Page 309: _refine_ls_number_reflns 4736 _refi
Page 313 and 314: C4 0.025(4) 0.019(4) 0.018(4) 0.001
Page 315 and 316: loop_ _geom_bond_atom_site_label_1
Page 317 and 318: C9 C4 C1 107.1(5) . . ? C10 C4 C1 1
Page 319 and 320: C36 C38 H38A 109.5 . . ? C36 C38 H3
Page 321 and 322: C29 C30 C36 C37 -90.4(7) . . . . ?
Page 323 and 324: The structure was solved by the dir
Page 325 and 326: _reflns_number_total 2447 _reflns_n
Page 327 and 328: C7 C 1.1671(4) 0.7629(7) 1.2254(4)
Page 329 and 330: C3 0.015(3) 0.016(3) 0.021(3) -0.00
Page 331 and 332: C21 H21A 0.9800 . ? C21 H21B 0.9800
Page 333 and 334: H21A C21 H21C 109.5 . . ? H21B C21
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