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

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C1 C4 C5 C11 64.4(7) . . . . ? C11 C5 C6 O2 42.6(7) . . . . ? C4 C5 C6 O2 177.1(5) . . . . ? C11 C5 C6 C7 161.8(5) . . . . ? C4 C5 C6 C7 -63.7(6) . . . . ? O2 C6 C7 O3 -75.2(6) . . . . ? C5 C6 C7 O3 163.1(5) . . . . ? O2 C6 C7 C8 165.4(5) . . . . ? C5 C6 C7 C8 43.7(7) . . . . ? O3 C7 C8 C9 -133.1(7) . . . . ? C6 C7 C8 C9 -10.2(9) . . . . ? C7 C8 C9 C4 -3.8(10) . . . . ? C10 C4 C9 C8 -137.2(7) . . . . ? C1 C4 C9 C8 106.9(8) . . . . ? C5 C4 C9 C8 -15.8(9) . . . . ? C6 C5 C11 C13 -90.0(7) . . . . ? C4 C5 C11 C13 138.3(6) . . . . ? C6 C5 C11 C12 35.1(8) . . . . ? C4 C5 C11 C12 -96.5(7) . . . . ? O1 C2 C14 C15 127.8(7) . . . . ? C3 C2 C14 C15 -116.5(7) . . . . ? O1 C2 C14 C19 -54.2(8) . . . . ? C3 C2 C14 C19 61.6(9) . . . . ? C19 C14 C15 C16 1.4(11) . . . . ? C2 C14 C15 C16 179.4(6) . . . . ? C14 C15 C16 C17 -0.6(12) . . . . ? C15 C16 C17 C18 -0.5(13) . . . . ? C16 C17 C18 C19 0.8(13) . . . . ? C15 C14 C19 C18 -1.1(12) . . . . ? C2 C14 C19 C18 -179.2(7) . . . . ? C17 C18 C19 C14 0.0(12) . . . . ? N1 C3 C20 C25 -10.5(9) . . . . ? C2 C3 C20 C25 110.5(7) . . . . ? N1 C3 C20 C21 165.3(6) . . . . ? C2 C3 C20 C21 -73.7(8) . . . . ? C25 C20 C21 C22 2.0(10) . . . . ? C3 C20 C21 C22 -174.0(6) . . . . ? C20 C21 C22 C23 0.6(10) . . . . ? C21 C22 C23 C24 -3.5(10) . . . . ? C22 C23 C24 C25 3.7(10) . . . . ? C21 C20 C25 C24 -1.7(10) . . . . ? C3 C20 C25 C24 174.1(6) . . . . ? C23 C24 C25 C20 -1.1(10) . . . . ? O4 C27 C28 N2 -6.0(6) . . . . ? C39 C27 C28 N2 -124.2(6) . . . . ? O4 C27 C28 C45 -131.4(6) . . . . ? C39 C27 C28 C45 110.4(7) . . . . ? N2 C26 C29 C34 -11.6(9) . . . . ? O4 C26 C29 C34 163.0(5) . . . . ? N2 C26 C29 C35 -127.3(7) . . . . ? O4 C26 C29 C35 47.3(8) . . . . ? N2 C26 C29 C30 108.4(7) . . . . ? O4 C26 C29 C30 -77.0(7) . . . . ? C26 C29 C30 C31 -67.1(7) . . . . ? C34 C29 C30 C31 51.7(7) . . . . ? C35 C29 C30 C31 169.9(5) . . . . ? C26 C29 C30 C36 67.2(7) . . . . ? C34 C29 C30 C36 -174.0(5) . . . . ? C35 C29 C30 C36 -55.8(7) . . . . ? C36 C30 C31 O5 39.7(7) . . . . ? C29 C30 C31 O5 174.0(5) . . . . ? C36 C30 C31 C32 159.3(5) . . . . ? C29 C30 C31 C32 -66.4(7) . . . . ? O5 C31 C32 O6 -75.2(6) . . . . ? C30 C31 C32 O6 163.2(5) . . . . ? O5 C31 C32 C33 166.0(5) . . . . ? C30 C31 C32 C33 44.4(7) . . . . ? O6 C32 C33 C34 -134.3(6) . . . . ? C31 C32 C33 C34 -11.6(9) . . . . ? C32 C33 C34 C29 -0.8(10) . . . . ? C26 C29 C34 C33 103.1(7) . . . . ? C35 C29 C34 C33 -140.4(6) . . . . ? C30 C29 C34 C33 -20.0(9) . . . . ? C31 C30 C36 C38 -87.8(7) . . . . ? C29 C30 C36 C38 141.4(6) . . . . ? C31 C30 C36 C37 40.3(8) . . . . ? 321
C29 C30 C36 C37 -90.4(7) . . . . ? O4 C27 C39 C40 -44.7(9) . . . . ? C28 C27 C39 C40 71.2(8) . . . . ? O4 C27 C39 C44 136.0(7) . . . . ? C28 C27 C39 C44 -108.1(8) . . . . ? C44 C39 C40 C41 2.3(11) . . . . ? C27 C39 C40 C41 -177.1(7) . . . . ? C39 C40 C41 C42 -1.7(11) . . . . ? C40 C41 C42 C43 1.3(12) . . . . ? C41 C42 C43 C44 -1.6(13) . . . . ? C42 C43 C44 C39 2.2(13) . . . . ? C40 C39 C44 C43 -2.5(12) . . . . ? C27 C39 C44 C43 176.8(7) . . . . ? N2 C28 C45 C50 5.5(10) . . . . ? C27 C28 C45 C50 125.8(7) . . . . ? N2 C28 C45 C46 -177.1(6) . . . . ? C27 C28 C45 C46 -56.8(8) . . . . ? C50 C45 C46 C47 1.7(11) . . . . ? C28 C45 C46 C47 -175.9(6) . . . . ? C45 C46 C47 C48 0.7(11) . . . . ? C46 C47 C48 C49 -1.1(11) . . . . ? C47 C48 C49 C50 -0.8(11) . . . . ? C46 C45 C50 C49 -3.6(11) . . . . ? C28 C45 C50 C49 173.8(6) . . . . ? C48 C49 C50 C45 3.2(11) . . . . ? O1 C1 N1 C3 -4.9(9) . . . . ? C4 C1 N1 C3 171.7(6) . . . . ? C20 C3 N1 C1 140.6(6) . . . . ? C2 C3 N1 C1 12.8(7) . . . . ? O4 C26 N2 C28 -0.2(8) . . . . ? C29 C26 N2 C28 174.3(6) . . . . ? C45 C28 N2 C26 130.2(6) . . . . ? C27 C28 N2 C26 4.0(7) . . . . ? N1 C1 O1 C2 -5.6(8) . . . . ? C4 C1 O1 C2 177.5(5) . . . . ? C14 C2 O1 C1 136.2(6) . . . . ? C3 C2 O1 C1 12.9(6) . . . . ? N2 C26 O4 C27 -3.9(8) . . . . ? C29 C26 O4 C27 -178.9(5) . . . . ? C39 C27 O4 C26 128.6(6) . . . . ? C28 C27 O4 C26 5.9(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2A O6 0.84 2.08 2.761(6) 137.9 1_545 O3 H3A N2 0.84 2.11 2.883(7) 152.0 1_545 O6 H6A O2 0.84 2.13 2.761(6) 131.7 1_565 O5 H5A O3 0.84 2.26 2.793(6) 121.1 1_465 _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.884 _refine_diff_density_max 0.242 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.055 322
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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 3H, OB
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Experimental for chapter 4.2 (1S*,2
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Experimental for chapter 4.2 10.0,
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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 and 318: C9 C4 C1 107.1(5) . . ? C10 C4 C1 1
Page 319: C36 C38 H38A 109.5 . . ? C36 C38 H3
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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