Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction.
Kamimura, Akio; Miyazaki, Koichiro; Suzuki, Shuzo; Ishikawa, Shingo; Uno, Hidemitsu; Organic & biomolecular chemistry 10 (2012) 4362–4366; doi:10.1039/c2ob25386k

data_7152383
_publ_section_title
;
 Total synthesis of ent-calystegine B4 via nitro-Michael/aldol reaction.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4362
_journal_page_last               4366
_journal_paper_doi               10.1039/c2ob25386k
_journal_volume                  10
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H25 N O6'
_chemical_formula_sum            'C15 H25 N O6'
_chemical_formula_weight         315.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.0621(18)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   10.8043(4)
_cell_length_b                   5.7743(2)
_cell_length_c                   14.0245(5)
_cell_measurement_reflns_used    5912
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.10
_cell_measurement_theta_min      3.36
_cell_volume                     821.86(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9427
_diffrn_reflns_theta_full        68.10
_diffrn_reflns_theta_max         68.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             340.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.200
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1196 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.11(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2849
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                2555
_reflns_number_total             2849
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c2ob25386k.txt
_cod_data_source_block           201000912
_cod_original_cell_volume        821.85(5)
_cod_database_code               7152383