Total Synthesis of Abyssomicin C, Atrop-abyssomicin C, and Abyssomicin D: Implications for Natural Origins of Atrop-abyssomicin C
K. C. Nicolaou; Scott T. Harrison; Journal of the American Chemical Society 129 (2007) 429–440; doi:10.1021/ja067083p

data_4108975
_publ_section_title
;
 Total Synthesis of Abyssomicin C, Atrop-abyssomicin C, and Abyssomicin D:
 Implications for Natural Origins of Atrop-abyssomicin C
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              429
_journal_page_last               440
_journal_paper_doi               10.1021/ja067083p
_journal_volume                  129
_journal_year                    2007
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(C21 H26 O5 S2), C H Cl2'
_chemical_formula_sum            'C43 H53 Cl2 O10 S4'
_chemical_formula_weight         929.03
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   19.187(4)
_cell_length_b                   9.2491(18)
_cell_length_c                   12.923(3)
_cell_measurement_reflns_used    6318
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.00
_cell_measurement_theta_min      2.50
_cell_volume                     2248.5(9)
_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, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8279
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.386
_exptl_absorpt_correction_T_max  0.9268
_exptl_absorpt_correction_T_min  0.8865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       Parallalepiped
_exptl_crystal_F_000             978
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.806
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3950
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.7000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                3695
_reflns_number_total             3950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067083psi20061006_105240.cif
_cod_data_source_block           shar
_cod_original_sg_symbol_Hall     'C 2yb'
_cod_database_code               4108975