Enantioselective Total Synthesis of Avrainvillamide and the Stephacidins
Phil S. Baran; Benjamin D. Hafensteiner; Narendra B. Ambhaikar; Carlos A. Guerrero; John D. Gallagher; Journal of the American Chemical Society 128 (2006) 8678–8693; doi:10.1021/ja061660s

data_4110696
_publ_section_title
;
 Enantioselective Total Synthesis of Avrainvillamide and the Stephacidins
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8678
_journal_page_last               8693
_journal_paper_doi               10.1021/ja061660s
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C29 H37 N3 O8'
_chemical_formula_weight         555.62
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.32(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.869(3)
_cell_length_b                   7.4858(15)
_cell_length_c                   14.598(3)
_cell_measurement_reflns_used    772
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.61
_cell_measurement_theta_min      2.87
_cell_volume                     1474.8(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_sigmaI/netI    0.2254
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8861
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.43
_diffrn_standards_decay_%        <1%
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1999)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_meas      0
_exptl_crystal_description       Needle-shaped
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5149
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.2418
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1469
_reflns_number_gt                1847
_reflns_number_total             5149
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja061660ssi20060328_112410.cif
_cod_data_source_block           emrg
_cod_original_cell_volume        1474.7(5)
_cod_database_code               4110696