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_4028713
_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 ad
_chemical_formula_moiety         'C35 H56 O5 Si2'
_chemical_formula_sum            'C35 H56 O5 Si2'
_chemical_formula_weight         612.987
_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                C35H56O5Si2_fx241_trauner
_audit_creation_date
;
'Sun Jun 20 10:55:16 2010'
;
_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                   8.7850(3)
_cell_length_b                   10.6361(4)
_cell_length_c                   38.7310(19)
_cell_measurement_reflns_used    11009
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.3346
_cell_measurement_theta_min      4.1329
_cell_volume                     3619.0(3)
_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
;
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      173(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
1 omega -70.00 -40.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- -28.6994 119.0000 -140.0000 30

2 omega -3.00 102.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 29.7932 77.0000 30.0000 105

3 omega 59.00 110.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 29.7932 179.0000 -90.0000 51

4 omega 57.00 110.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 29.7932 179.0000 30.0000 53

5 omega 16.00 86.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 29.7932 -119.0000 140.0000 70

6 omega 21.00 91.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 29.7932 77.0000 -120.0000 70

7 omega -45.00 91.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 29.7932 0.0000 60.0000 136

;
_diffrn_measurement_device       'CCD camera on \k-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0016058192
_diffrn_orient_matrix_UB_12      -0.0092136775
_diffrn_orient_matrix_UB_13      0.0181418906
_diffrn_orient_matrix_UB_21      0.0771234327
_diffrn_orient_matrix_UB_22      0.0191617954
_diffrn_orient_matrix_UB_23      0.0011067503
_diffrn_orient_matrix_UB_31      -0.0237007658
_diffrn_orient_matrix_UB_32      0.0631493640
_diffrn_orient_matrix_UB_33      0.0023194624
_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  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            43906
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.41
_diffrn_reflns_theta_min         4.14
_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    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86410
_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    1.12507(9)
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         11978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0509
_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^)+(0.0453P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1001
_reflns_number_gt                7653
_reflns_number_total             11978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401706r_si_002_8.cif
_cod_data_source_block           fx241
_cod_database_code               4028713