Total Synthesis of (±)-α-Isosparteine, (±)-β-Isosparteine, and (±)-Sparteine from a Common Tetraoxobispidine Intermediate
Neil R. Norcross; John P. Melbardis; Margarita Ferris Solera; Mark A. Sephton; Colin Kilner; Lev N. Zakharov; Peter C. Astles; Stuart L. Warriner; Paul R. Blakemore; Journal of Organic Chemistry 73 (2008) 7939–7951; doi:10.1021/jo8013512

data_4023732
_publ_section_title
;
 Total Synthesis of (+-)-\a-Isosparteine, (+-)-\b-Isosparteine, and
 (+-)-Sparteine from a Common Tetraoxobispidine Intermediate
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7939
_journal_page_last               7951
_journal_paper_doi               10.1021/jo8013512
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C7 H6 N2 O4'
_chemical_formula_weight         182.14
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.3597(3)
_cell_length_b                   12.0086(7)
_cell_length_c                   18.7931(10)
_cell_measurement_reflns_used    5249
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      3.56
_cell_volume                     1435.25(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12015
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0593P)^2^+0.4569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                1602
_reflns_number_total             1744
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8013512_si_003.cif
_cod_data_source_block           cmpd22
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_database_code               4023732