Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids–first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine.
Gruner, Konstanze K.; Hopfmann, Thomas; Matsumoto, Kazuhiro; Jäger, Anne; Katsuki, Tsutomu; Knölker, Hans-Joachim; Organic & biomolecular chemistry 9 (2011) 2057–2061; doi:10.1039/c0ob01088j

data_7151813
_publ_section_title
;
 Efficient iron-mediated approach to pyrano[3,2-a]carbazole
 alkaloids--first total syntheses of O-methylmurrayamine A and
 7-methoxymurrayacine, first asymmetric synthesis and assignment of the
 absolute configuration of (-)-trans-dihydroxygirinimbine.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2057
_journal_page_last               2061
_journal_paper_doi               10.1039/c0ob01088j
_journal_volume                  9
_journal_year                    2011
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C18 H17 N O'
_chemical_formula_sum            'C18 H17 N O'
_chemical_formula_weight         263.33
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_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                 109.03(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.960(2)
_cell_length_b                   16.344(3)
_cell_length_c                   7.655(2)
_cell_measurement_reflns_used    533
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      24.754
_cell_measurement_theta_min      4.026
_cell_volume                     1414.6(6)
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       \f
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            24148
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bock
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3367
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0457P)^2^+0.0152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                2602
_reflns_number_total             3367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01088j.txt
_cod_data_source_block           an147
_cod_original_cell_volume        1414.6(5)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7151813