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_4124293
_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 syn
_chemical_formula_sum            'C21 H31 N O2'
_chemical_formula_weight         329.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-02-10 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5106(9)
_cell_length_b                   16.465(3)
_cell_length_c                   17.701(3)
_cell_measurement_reflns_used    4554
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.24
_cell_measurement_theta_min      5.00
_cell_volume                     1897.5(5)
_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 0.884
_diffrn_measured_fraction_theta_max 0.996
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.884
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6944
_diffrn_reflns_point_group_measured_fraction_full 0.873
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.264
_diffrn_reflns_theta_min         4.997
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.7521
_exptl_absorpt_correction_T_min  0.5491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       lath
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.687
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
; 
 Flack x determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.25(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0351
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.2376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    0.859
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2741
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b07710_si_003.cif
_cod_data_source_block           n3300_2m
_cod_depositor_comments
'Adding full bibliography for 4124293--4124295.cif.'
_cod_original_cell_volume        1897.4(5)
_cod_database_code               4124293
_shelx_estimated_absorpt_t_min   0.697
_shelx_estimated_absorpt_t_max   0.988
_shelxl_version_number           2013-3
_shelx_res_checksum              71692
_shelx_hkl_checksum              57581