Short, Stereoselective Synthesis of the Naturally Occurring Pyrrolidine Radicamine B and a Formal Synthesis of Nectrisine
Celia Ribes; Eva Falomir; Miguel Carda; J. Alberto Marco; Journal of Organic Chemistry 73 (2008) 7779–7782; doi:10.1021/jo8012989

data_4023709
_publ_contact_author_address
;Departament de Quimica Inorganica i Organica (ESTCE)
Universitat Jaume I
Av. Sos Baynat s/n 12071
Castello (SPAIN)
;
_publ_contact_author_email       sdiaz@qio.uji.es
_publ_contact_author_fax         '+34 964 72 8214'
_publ_contact_author_name        'Santiago Diaz Oltra'
_publ_contact_author_phone       '+34 964 72 8225'
_publ_section_title
;
 Short, Stereoselective Synthesis of the Naturally Occurring Pyrrolidine
 Radicamine B and a Formal Synthesis of Nectrisine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7779
_journal_page_last               7782
_journal_paper_doi               10.1021/jo8012989
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C18 H31 N O7'
_chemical_formula_sum            'C18 H31 N O7'
_chemical_formula_weight         373.44
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   10.6646(5)
_cell_length_b                   13.0545(5)
_cell_length_c                   15.2913(6)
_cell_measurement_temperature    571(2)
_cell_volume                     2128.87(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      571(2)
_diffrn_measured_fraction_theta_full 0.473
_diffrn_measured_fraction_theta_max 0.473
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8907
_diffrn_reflns_theta_full        30.54
_diffrn_reflns_theta_max         30.54
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.003
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0685P)^2^+0.2525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1701
_reflns_number_total             2998
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8012989_si_001.cif
_cod_data_source_block           str906m
_cod_database_code               4023709