Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction: Application to Total Synthesis of Lamellarins H and D
B. Manjappa, Kiran; Lin, Jhih-Min; Yang, Ding-Yah; The Journal of Organic Chemistry  (2017) –; doi:10.1021/acs.joc.7b01061

data_4032605
_publ_section_title
;
 Construction of Pentacyclic Lamellarin Skeleton via Grob Reaction:
 Application to Total Synthesis of Lamellarins H and D
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.7b01061
_journal_year                    2017
_chemical_formula_moiety         'C28 H21 N O8, 2(C2 H6 O S)'
_chemical_formula_sum            'C32 H33 N O10 S2'
_chemical_formula_weight         655.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                65.188(2)
_cell_angle_beta                 77.413(2)
_cell_angle_gamma                86.050(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0377(7)
_cell_length_b                   13.8122(10)
_cell_length_c                   14.1416(9)
_cell_measurement_reflns_used    8133
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.271
_cell_measurement_theta_min      2.965
_cell_volume                     1563.3(2)
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23829
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.965
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_correction_T_min  0.8605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     428
_refine_ls_number_reflns         6373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0783P)^2^+1.9494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4649
_reflns_number_total             6373
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01061_si_003.cif
_cod_data_source_block           bmk4540
_cod_database_code               4032605
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.916
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              27415
_shelx_hkl_checksum              13566