Total Synthesis of Malyngamides K, L, and 5''-epi-C and Absolute Configuration of Malyngamide L
Jun-Tao Zhang; Xian-Liang Qi; Jie Chen; Bao-Sheng Li; You-Bai Zhou; Xiao-Ping Cao; Journal of Organic Chemistry 76 (2011) 3946–3959; doi:10.1021/jo2003852

data_4026304
_publ_section_title
;
 Total Synthesis of Malyngamides K, L, and 5''-epi-C and Absolute
 Configuration of Malyngamide L
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3946
_journal_page_last               3959
_journal_paper_doi               10.1021/jo2003852
_journal_volume                  76
_journal_year                    2011
_chemical_absolute_configuration none
_chemical_formula_sum            'C9 H13 Br O3'
_chemical_formula_weight         249.10
_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                 113.038(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9066(15)
_cell_length_b                   8.1505(11)
_cell_length_c                   12.4120(18)
_cell_measurement_reflns_used    1576
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.38
_cell_measurement_theta_min      3.07
_cell_volume                     1015.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0788
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5701
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    4.022
_exptl_absorpt_correction_T_max  0.3334
_exptl_absorpt_correction_T_min  0.2829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0160P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                2803
_reflns_number_total             3897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2003852_si_001.cif
_cod_data_source_block           p21
_cod_original_cell_volume        1015.4(2)
_cod_database_code               4026304