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_4028708
_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         'C20 H30 O9'
_chemical_formula_sum            'C20 H30 O9'
_chemical_formula_weight         414.447
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C20H30O9_no167_trauner
_audit_creation_date
;
'Tue Sep 08 13:31:22 2009'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             14-Sep-09
_cell_angle_alpha                90.00
_cell_angle_beta                 90.165(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   10.7518(3)
_cell_length_b                   17.8960(6)
_cell_length_c                   16.0933(4)
_cell_measurement_reflns_used    10363
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.2497
_cell_measurement_theta_min      4.2356
_cell_volume                     3096.57(16)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_collection
;
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.,
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(compiled May 6 2009,17:20:42)
;
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)'
_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      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
1 omega 8.00 52.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -20.8400 77.0000 -90.0000 44

2 omega -54.00 49.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -20.8400 77.0000 -120.0000 103

3 omega -51.00 43.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -20.8400 77.0000 150.0000 94

4 omega -12.00 53.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 21.0744 77.0000 120.0000 65

5 omega 65.00 93.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 21.0744 77.0000 30.0000 28

6 omega -12.00 86.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 21.0744 77.0000 0.0000 98

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       'omega scans'
_diffrn_orient_matrix_UB_11      -0.0656828621
_diffrn_orient_matrix_UB_12      -0.0010846507
_diffrn_orient_matrix_UB_13      0.0036306572
_diffrn_orient_matrix_UB_21      0.0023926719
_diffrn_orient_matrix_UB_22      -0.0434506072
_diffrn_orient_matrix_UB_23      0.0063705225
_diffrn_orient_matrix_UB_31      0.0057022311
_diffrn_orient_matrix_UB_32      0.0072080095
_diffrn_orient_matrix_UB_33      0.0389447370
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23608
_diffrn_reflns_theta_full        26.33
_diffrn_reflns_theta_max         26.33
_diffrn_reflns_theta_min         4.24
_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    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99210
_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    1.33350(7)
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(5)
_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     796
_refine_ls_number_reflns         6461
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.877
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0311P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0532
_refine_ls_wR_factor_ref         0.0554
_reflns_number_gt                4858
_reflns_number_total             6461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401706r_si_002_3.cif
_cod_data_source_block           no167
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028708