Lobatamide C: Total Synthesis, Stereochemical Assignment, Preparation of Simplified Analogues, and V-ATPase Inhibition Studies
Ruichao Shen; Cheng Ting Lin; Emma Jean Bowman; Barry J. Bowman; John A. Porco; Journal of the American Chemical Society 125 (2003) 7889–7901; doi:10.1021/ja0352350

data_4113866
_publ_section_title
;
 Lobatamide C: Total Synthesis, Stereochemical Assignment, Preparation of
 Simplified Analogues, and V-ATPase Inhibition Studies
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7889
_journal_page_last               7901
_journal_paper_doi               10.1021/ja0352350
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C41 H51 Br N2 O9 S'
_chemical_formula_weight         827.81
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.538(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.8954(15)
_cell_length_b                   8.8330(13)
_cell_length_c                   24.243(3)
_cell_measurement_reflns_used    5490
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.53
_cell_volume                     2114.9(5)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker 1K CCD area detector'
_diffrn_measurement_method       '0.3 deg. omega scans'
_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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13032
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    1.075
_exptl_absorpt_correction_T_max  0.9736
_exptl_absorpt_correction_T_min  0.6731
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      0
_exptl_crystal_description       plate
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         7052
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.376
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0837P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                5426
_reflns_number_total             7052
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0352350si20030319_105425.cif
_cod_data_source_block           porco19
_cod_database_code               4113866