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

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C21 C3 H3 109.7 . . ? C2 C3 H3 109.7 . . ? C1 C4 C9 109.98(15) . . ? C1 C4 C10 106.90(14) . . ? C9 C4 C10 107.64(15) . . ? C1 C4 C5 111.49(14) . . ? C9 C4 C5 112.12(14) . . ? C10 C4 C5 108.48(15) . . ? C6 C5 C11 112.60(14) . . ? C6 C5 C4 108.95(14) . . ? C11 C5 C4 115.11(14) . . ? C6 C5 H5 106.5 . . ? C11 C5 H5 106.5 . . ? C4 C5 H5 106.5 . . ? C7 C6 O2 125.65(15) . . ? C7 C6 C5 122.94(16) . . ? O2 C6 C5 111.41(15) . . ? C6 C7 C8 119.48(15) . . ? C6 C7 H7 120.3 . . ? C8 C7 H7 120.3 . . ? C9 C8 C7 121.53(17) . . ? C9 C8 H8 119.2 . . ? C7 C8 H8 119.2 . . ? C8 C9 C4 120.30(17) . . ? C8 C9 H9 119.9 . . ? C4 C9 H9 119.9 . . ? C4 C10 H10A 109.5 . . ? C4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C13 110.37(15) . . ? C12 C11 C5 115.00(14) . . ? C13 C11 C5 111.50(14) . . ? C12 C11 H11 106.5 . . ? C13 C11 H11 106.5 . . ? C5 C11 H11 106.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 C14 H14A 109.5 . . ? O2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.93(16) . . ? C16 C15 C2 121.70(15) . . ? C20 C15 C2 119.29(16) . . ? C17 C16 C15 120.42(17) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 120.28(19) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 119.65(18) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.25(18) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C15 120.46(18) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? C22 C21 C26 119.32(16) . . ? C22 C21 C3 119.08(16) . . ? 303
C26 C21 C3 121.41(15) . . ? C23 C22 C21 120.59(17) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C22 C23 C24 120.03(17) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 119.47(17) . . ? C25 C24 H24 120.3 . . ? C23 C24 H24 120.3 . . ? C24 C25 C26 120.76(18) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 119.81(17) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 O1 -2.4(2) . . . . ? C2 N1 C1 C4 173.89(16) . . . . ? C3 O1 C1 N1 -0.3(2) . . . . ? C3 O1 C1 C4 -177.07(14) . . . . ? C1 N1 C2 C15 127.44(16) . . . . ? C1 N1 C2 C3 3.88(18) . . . . ? C1 O1 C3 C21 124.14(15) . . . . ? C1 O1 C3 C2 2.73(17) . . . . ? N1 C2 C3 O1 -3.96(16) . . . . ? C15 C2 C3 O1 -127.78(14) . . . . ? N1 C2 C3 C21 -124.49(15) . . . . ? C15 C2 C3 C21 111.69(16) . . . . ? N1 C1 C4 C9 -3.8(2) . . . . ? O1 C1 C4 C9 172.64(14) . . . . ? N1 C1 C4 C10 -120.4(2) . . . . ? O1 C1 C4 C10 56.1(2) . . . . ? N1 C1 C4 C5 121.23(19) . . . . ? O1 C1 C4 C5 -62.34(19) . . . . ? C1 C4 C5 C6 -166.51(14) . . . . ? C9 C4 C5 C6 -42.70(19) . . . . ? C10 C4 C5 C6 76.04(17) . . . . ? C1 C4 C5 C11 -38.9(2) . . . . ? C9 C4 C5 C11 84.87(18) . . . . ? C10 C4 C5 C11 -156.39(15) . . . . ? C14 O2 C6 C7 -0.5(3) . . . . ? C14 O2 C6 C5 179.64(14) . . . . ? C11 C5 C6 C7 -98.17(19) . . . . ? C4 C5 C6 C7 30.8(2) . . . . ? C11 C5 C6 O2 81.72(18) . . . . ? C4 C5 C6 O2 -149.32(14) . . . . ? O2 C6 C7 C8 176.77(16) . . . . ? C5 C6 C7 C8 -3.4(3) . . . . ? C6 C7 C8 C9 -12.4(3) . . . . ? C7 C8 C9 C4 -3.7(3) . . . . ? C1 C4 C9 C8 156.95(17) . . . . ? C10 C4 C9 C8 -86.9(2) . . . . ? C5 C4 C9 C8 32.3(2) . . . . ? C6 C5 C11 C12 66.75(19) . . . . ? C4 C5 C11 C12 -58.95(19) . . . . ? C6 C5 C11 C13 -59.9(2) . . . . ? C4 C5 C11 C13 174.44(15) . . . . ? N1 C2 C15 C16 -35.3(2) . . . . ? C3 C2 C15 C16 83.3(2) . . . . ? N1 C2 C15 C20 147.76(16) . . . . ? C3 C2 C15 C20 -93.66(19) . . . . ? C20 C15 C16 C17 -0.1(3) . . . . ? C2 C15 C16 C17 -177.07(17) . . . . ? C15 C16 C17 C18 0.2(3) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? 304
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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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Page 269 and 270: Experimental for chapter 4.2 cm 3 )
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: C2 H2 1.0000 . ? C3 C21 1.506(2) .
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 and 310: _refine_ls_number_reflns 4736 _refi
Page 311 and 312: H25 H 0.7979 0.2335 0.3365 0.028 Ui
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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