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_4108974
_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         'C19 H22 O6'
_chemical_formula_sum            'C19 H22 O6'
_chemical_formula_weight         346.37
_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                 93.88(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.934(4)
_cell_length_b                   6.8950(14)
_cell_length_c                   12.745(3)
_cell_measurement_reflns_used    3499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      5.00
_cell_volume                     1835.4(7)
_computing_cell_refinement       'Bruker SMART'
_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  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6578
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_diffrn_standards_decay_%        1
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.1200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2572
_reflns_number_total             3192
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja067083psi20061006_105220.cif
_cod_data_source_block           stha
_cod_database_code               4108974