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

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C20 C21 H21 119.7 . . ? C21 C22 C23 121.1(7) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C22 C23 C24 119.2(7) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? C25 C24 C23 119.1(7) . . ? C25 C24 H24 120.4 . . ? C23 C24 H24 120.4 . . ? C20 C25 C24 121.6(7) . . ? C20 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? N2 C26 O4 118.2(6) . . ? N2 C26 C29 125.4(6) . . ? O4 C26 C29 116.1(6) . . ? O4 C27 C39 108.2(5) . . ? O4 C27 C28 104.2(5) . . ? C39 C27 C28 114.9(6) . . ? O4 C27 H27 109.8 . . ? C39 C27 H27 109.8 . . ? C28 C27 H27 109.8 . . ? N2 C28 C45 113.8(5) . . ? N2 C28 C27 104.3(5) . . ? C45 C28 C27 115.1(6) . . ? N2 C28 H28 107.8 . . ? C45 C28 H28 107.8 . . ? C27 C28 H28 107.8 . . ? C26 C29 C34 106.7(5) . . ? C26 C29 C35 108.7(5) . . ? C34 C29 C35 107.6(6) . . ? C26 C29 C30 113.7(6) . . ? C34 C29 C30 108.8(5) . . ? C35 C29 C30 111.1(5) . . ? C31 C30 C36 116.6(5) . . ? C31 C30 C29 108.8(5) . . ? C36 C30 C29 116.6(5) . . ? C31 C30 H30 104.4 . . ? C36 C30 H30 104.4 . . ? C29 C30 H30 104.4 . . ? O5 C31 C32 107.9(5) . . ? O5 C31 C30 111.3(5) . . ? C32 C31 C30 110.1(6) . . ? O5 C31 H31 109.2 . . ? C32 C31 H31 109.2 . . ? C30 C31 H31 109.2 . . ? O6 C32 C33 105.7(5) . . ? O6 C32 C31 112.5(6) . . ? C33 C32 C31 111.9(5) . . ? O6 C32 H32 108.9 . . ? C33 C32 H32 108.9 . . ? C31 C32 H32 108.9 . . ? C34 C33 C32 125.0(6) . . ? C34 C33 H33 117.5 . . ? C32 C33 H33 117.5 . . ? C33 C34 C29 122.3(6) . . ? C33 C34 H34 118.8 . . ? C29 C34 H34 118.8 . . ? C29 C35 H35A 109.5 . . ? C29 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C29 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C38 C36 C37 111.2(6) . . ? C38 C36 C30 111.0(6) . . ? C37 C36 C30 116.0(5) . . ? C38 C36 H36 106.0 . . ? C37 C36 H36 106.0 . . ? C30 C36 H36 106.0 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? 319
C36 C38 H38A 109.5 . . ? C36 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C36 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 C44 119.2(7) . . ? C40 C39 C27 120.9(6) . . ? C44 C39 C27 119.9(7) . . ? C39 C40 C41 121.2(7) . . ? C39 C40 H40 119.4 . . ? C41 C40 H40 119.4 . . ? C42 C41 C40 118.4(8) . . ? C42 C41 H41 120.8 . . ? C40 C41 H41 120.8 . . ? C43 C42 C41 120.7(8) . . ? C43 C42 H42 119.7 . . ? C41 C42 H42 119.7 . . ? C42 C43 C44 121.0(8) . . ? C42 C43 H43 119.5 . . ? C44 C43 H43 119.5 . . ? C43 C44 C39 119.5(8) . . ? C43 C44 H44 120.2 . . ? C39 C44 H44 120.2 . . ? C50 C45 C46 118.9(7) . . ? C50 C45 C28 122.0(6) . . ? C46 C45 C28 119.0(6) . . ? C47 C46 C45 120.0(7) . . ? C47 C46 H46 120.0 . . ? C45 C46 H46 120.0 . . ? C46 C47 C48 122.3(7) . . ? C46 C47 H47 118.8 . . ? C48 C47 H47 118.8 . . ? C47 C48 C49 118.2(7) . . ? C47 C48 H48 120.9 . . ? C49 C48 H48 120.9 . . ? C50 C49 C48 119.1(7) . . ? C50 C49 H49 120.4 . . ? C48 C49 H49 120.4 . . ? C45 C50 C49 121.3(7) . . ? C45 C50 H50 119.3 . . ? C49 C50 H50 119.3 . . ? C1 N1 C3 105.5(5) . . ? C26 N2 C28 107.3(6) . . ? C1 O1 C2 104.1(5) . . ? C6 O2 H2A 109.5 . . ? C7 O3 H3A 109.5 . . ? C26 O4 C27 105.7(5) . . ? C31 O5 H5A 109.5 . . ? C32 O6 H6A 109.5 . . ? 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 O1 C2 C3 N1 -15.7(6) . . . . ? C14 C2 C3 N1 -133.9(6) . . . . ? O1 C2 C3 C20 -140.9(6) . . . . ? C14 C2 C3 C20 100.9(7) . . . . ? N1 C1 C4 C9 -5.2(9) . . . . ? O1 C1 C4 C9 171.5(6) . . . . ? N1 C1 C4 C10 -121.1(7) . . . . ? O1 C1 C4 C10 55.7(7) . . . . ? N1 C1 C4 C5 115.1(7) . . . . ? O1 C1 C4 C5 -68.1(7) . . . . ? C9 C4 C5 C6 48.6(7) . . . . ? C10 C4 C5 C6 167.7(5) . . . . ? C1 C4 C5 C6 -70.5(6) . . . . ? C9 C4 C5 C11 -176.5(5) . . . . ? C10 C4 C5 C11 -57.4(7) . . . . ? 320
Page 1 and 2:
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 3H, OB
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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 )
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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 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: C9 C4 C1 107.1(5) . . ? C10 C4 C1 1
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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