Total Synthesis of the Galbulimima Alkaloids Himandravine and GB17 Using Biomimetic Diels-Alder Reactions of Double Diene Precursors.
Larson, Reed T.; Pemberton, Ryan P.; Franke, Jenna M.; Tantillo, Dean J.; Thomson, Regan J.; Journal of the American Chemical Society 137 (2015) 11197–11204; doi:10.1021/jacs.5b07710

data_4124360
_publ_section_title
;
 Total Synthesis of the Galbulimima Alkaloids Himandravine and GB17 Using
 Biomimetic Diels-Alder Reactions of Double Diene Precursors.
;
_journal_issue                   34
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11197
_journal_page_last               11204
_journal_paper_doi               10.1021/jacs.5b07710
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C28 H38 Cl N O3'
_chemical_formula_weight         472.04
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-03-06 # Formatted by publCIF
;
_cell_angle_alpha                97.3625(11)
_cell_angle_beta                 96.2287(11)
_cell_angle_gamma                90.2865(10)
_cell_formula_units_Z            2
_cell_length_a                   5.29851(10)
_cell_length_b                   10.6425(2)
_cell_length_c                   22.9174(5)
_cell_measurement_reflns_used    8577
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.95
_cell_measurement_theta_min      3.91
_cell_volume                     1273.84(4)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.928
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16619
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         65.051
_diffrn_reflns_theta_min         1.956
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, bruker'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       plate
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.006
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
; 
 Flack x determined using 3362 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.042(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         7978
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0262
_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^)+(0.0295P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0633
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.798
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                7599
_reflns_number_total             7978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b07710_si_001.cif
_cod_data_source_block           n3363_2m
_cod_database_code               4124360
_shelx_estimated_absorpt_t_min   0.752
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-3
_shelx_res_checksum              18442
_shelx_hkl_checksum              24119