Asymmetric Synthesis of the Highly Potent Anti-Metastatic Prostacyclin Analogue Cicaprost and Its Isomer Isocicaprost
Marco Lerm; Hans-Joachim Gais; Kejun Cheng; Cornelia Vermeeren; Journal of the American Chemical Society 125 (2003) 9653–9667; doi:10.1021/ja030200l

data_4114045
_publ_contact_author_address
;     Institut f\"ur Organische Chemie  
      Rheinisch-Westfa\"lische Technische Hochschule Aachen
      Professor-Pirlet-Strasse 1
      D-52074 Aachen
      Germany
;
_publ_contact_author_email       '     gais@rwth-aachen.de'
_publ_contact_author_fax         '     ++49 241 80 92385'
_publ_contact_author_name        '     Hans-Joachim Gais'
_publ_contact_author_phone       '     ++49 241 80 94710'
_publ_section_title
;
 Asymmetric Synthesis of the Highly Potent Anti-Metastatic Prostacyclin
 Analogue Cicaprost and Its Isomer Isocicaprost
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9653
_journal_page_last               9667
_journal_paper_doi               10.1021/ja030200l
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C14 H21 N O3'
_chemical_formula_weight         251.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_date             03-01-26
_audit_creation_method           Xtal3.7
_cell_angle_alpha                90.00000
_cell_angle_beta                 110.20(2)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            2
_cell_length_a                   5.727(2)
_cell_length_b                   17.490(3)
_cell_length_c                   6.955(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150
_cell_volume                     653.8(3)
_computing_data_reduction        'xtal DIFDAT SORTRF ADDREF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    xtal
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method
;
\w/2\q
;
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54179
_diffrn_reflns_av_R_equivalents  .076
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4888
_diffrn_reflns_theta_max         74.96
_diffrn_standards_decay_%        7
_diffrn_standards_interval_count 200
_exptl_absorpt_coefficient_mu    .721
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            '     colourless'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       '    irregular'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         .699
_refine_diff_density_min         -.43
_refine_ls_extinction_coef       .00000
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2343
_refine_ls_R_factor_gt           .09
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
w=1/[7.0\s(F)^2^]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .102
_reflns_Friedel_coverage         .939
_reflns_number_gt                2352
_reflns_number_total             2650
_reflns_threshold_expression     'I>  2.00 sig(I)'
_cod_data_source_file            ja030200l.cif
_cod_data_source_block           JA030200L
_cod_original_sg_symbol_Hall     p_2y1
_cod_original_formula_sum        'C14 H21 N1 O3'
_cod_database_code               4114045