Total Synthesis of Herbicidin C and Aureonuclemycin: Impasses and New Avenues
Dominik Hager; Christian Paulitz; Jörg Tiebes; Peter Mayer; Dirk Trauner; Journal of Organic Chemistry 78 (2013) 10784–10801; doi:10.1021/jo401706r

data_4028712
_publ_section_title
;
 Total Synthesis of Herbicidin C and Aureonuclemycin: Impasses and New
 Avenues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10784
_journal_page_last               10801
_journal_paper_doi               10.1021/jo401706r
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H14 O5'
_chemical_formula_sum            'C10 H14 O5'
_chemical_formula_weight         214.215
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C10H14O5_ex262_trauner
_audit_creation_date
;
'Sat May 30 21:33:44 2009'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             26-Jul-12
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1089(3)
_cell_length_b                   7.2805(3)
_cell_length_c                   20.2476(8)
_cell_measurement_reflns_used    5396
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.6578
_cell_measurement_theta_min      4.1152
_cell_volume                     1047.94(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
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;
_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
<i>Acta Cryst.</i> A<b>64</b>, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
1 omega 0.00 101.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 70.0000 0.0000 101

2 omega 0.00 101.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 70.0000 120.0000 101

3 omega 0.00 101.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 70.0000 240.0000 101

4 omega -41.00 60.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 -70.0000 0.0000 101

5 omega -41.00 60.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 -70.0000 120.0000 101

6 omega -41.00 60.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 -70.0000 240.0000 101

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0936900351
_diffrn_orient_matrix_UB_12      0.0330689735
_diffrn_orient_matrix_UB_13      -0.0025873196
_diffrn_orient_matrix_UB_21      -0.0078787940
_diffrn_orient_matrix_UB_22      -0.0000777632
_diffrn_orient_matrix_UB_23      0.0349637557
_diffrn_orient_matrix_UB_31      0.0336510123
_diffrn_orient_matrix_UB_32      0.0917660242
_diffrn_orient_matrix_UB_33      0.0009460359
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15607
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.73
_diffrn_reflns_theta_min         4.13
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.35778(9)
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0381P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                2560
_reflns_number_total             3595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401706r_si_002_7.cif
_cod_data_source_block           ex262
_cod_database_code               4028712