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_4105344
_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            'C18 H23 B N2 O4'
_chemical_formula_weight         342.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 105.697(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.2222(4)
_cell_length_b                   6.6121(1)
_cell_length_c                   19.9706(5)
_cell_measurement_reflns_used    32163
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      140.0
_cell_measurement_theta_min      7.0
_cell_volume                     3460.57(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-Axis Spider with Image Plate'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1265
_diffrn_reflns_av_sigmaI/netI    0.1842
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29423
_diffrn_reflns_theta_full        67.49
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         6.91
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor. T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       lath
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.00167(17)
_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   1.753
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     458
_refine_ls_number_reflns         6137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.753
_refine_ls_R_factor_all          0.2992
_refine_ls_R_factor_gt           0.1482
_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^)+(0.0300P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.2138
_reflns_number_gt                2372
_reflns_number_total             6137
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9085534_si_004.cif
_cod_data_source_block           shelxl
_cod_database_code               4105344