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_4028711
_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         'C29 H38 O8'
_chemical_formula_sum            'C29 H38 O8'
_chemical_formula_weight         514.607
_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                C29H38O8_pn104_trauner
_audit_creation_date             25-Mar-11
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             30-Mar-11
_cell_angle_alpha                90.00
_cell_angle_beta                 105.576(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.6591(6)
_cell_length_b                   5.2307(2)
_cell_length_c                   18.5204(8)
_cell_measurement_reflns_used    4808
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.350
_cell_measurement_theta_min      3.134
_cell_volume                     1367.94(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_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 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0482810
_diffrn_orient_matrix_UB_12      -0.1158683
_diffrn_orient_matrix_UB_13      -0.0118615
_diffrn_orient_matrix_UB_21      -0.0413722
_diffrn_orient_matrix_UB_22      -0.0217804
_diffrn_orient_matrix_UB_23      -0.0521814
_diffrn_orient_matrix_UB_31      0.0311841
_diffrn_orient_matrix_UB_32      0.1504977
_diffrn_orient_matrix_UB_33      -0.0166840
_diffrn_radiation_collimation    0.20
_diffrn_radiation_monochromator  'MONTEL, graded multilayered x-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_sigmaI/netI    0.0858
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9302
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.16
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.24938(9)
_exptl_crystal_description       rod
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.206
_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   -0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4873
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0356P)^2^+0.1295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                3634
_reflns_number_total             4873
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401706r_si_002_6.cif
_cod_data_source_block           pn104
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028711