Modified Julia-Kocienski Reagents for a Stereoselective Introduction of Trisubstituted Double Bonds: A Formal Total Synthesis of Limazepine E and Barmumycin.
Sakaine, Guna; Smits, Gints; The Journal of organic chemistry 83 (2018) 5323–5330; doi:10.1021/acs.joc.8b00643

data_4035509
_publ_section_title
;
 Modified Julia-Kocienski Reagents for a Stereoselective Introduction of
 Trisubstituted Double Bonds: A Formal Total Synthesis of Limazepine E and
 Barmumycin.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5323
_journal_page_last               5330
_journal_paper_doi               10.1021/acs.joc.8b00643
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H34 N4 O2 S'
_chemical_formula_sum            'C21 H34 N4 O2 S'
_chemical_formula_weight         406.58
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.9220(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7130(2)
_cell_length_b                   25.2530(6)
_cell_length_c                   9.8340(3)
_cell_measurement_reflns_used    3072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      0.9
_cell_volume                     2330.76(10)
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_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  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10034
_diffrn_reflns_theta_full        28.0
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         2.6
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1345
_refine_ls_R_factor_gt           0.0732
_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^)+(0.0855P)^2^+1.1780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.2033
_reflns_d_resolution_high        0.7615
_reflns_number_gt                3107
_reflns_number_total             5478
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00643_si_002.cif
_cod_data_source_block           GSAd115
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               4035509
_shelx_title                     ' Compound GSA-D-115'
_shelx_refln_list_code           4
_shelx_f_calc_maximum            119.34
_shelx_f_squared_multiplier      1.000