Concise Syntheses of (-)-Galanthamine and (\±)-Codeine via Intramolecular Alkylation of a Phenol Derivative
Philip Magnus; Neeraj Sane; Benjamin P. Fauber; Vince Lynch; Journal of the American Chemical Society 131 (2009) 16045–16047; doi:10.1021/ja9085534

data_4105346
_publ_section_title
;
 Concise Syntheses of (-)-Galanthamine and (\+-)-Codeine via
 Intramolecular Alkylation of a Phenol Derivative
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16045
_journal_page_last               16047
_journal_paper_doi               10.1021/ja9085534
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C19 H21 N O6'
_chemical_formula_weight         359.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.745(1)
_cell_angle_beta                 92.890(1)
_cell_angle_gamma                109.487(1)
_cell_formula_units_Z            2
_cell_length_a                   8.7189(2)
_cell_length_b                   9.8011(3)
_cell_length_c                   11.0087(3)
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     837.99(4)
_computing_cell_refinement       'Collect software, Nonius B.V. 1998'
_computing_data_collection       'Collect software, Nonius B.V. 1998'
_computing_data_reduction
;
DENZO and Scalepack (Otwinoski and Minor, 1997)
;
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_solution
;

SIR97 - Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C., 
Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R.
;
_diffrn_ambient_temperature      153(2)
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       \w-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  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6291
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plates
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0396P)^2^+0.2873P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1020
_reflns_number_gt                2919
_reflns_number_total             3820
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9085534_si_006.cif
_cod_data_source_block           mor189
_cod_database_code               4105346