Concise Stereocontrolled Formal Synthesis of (\±)-Quinine and Total Synthesis of (\±)-7- Hydroxyquinine via Merged Morita‒Baylis‒Hillman‒Tsuji‒Trost Cyclization
Peter Webber; Michael J. Krische; Journal of Organic Chemistry 73 (2008) 9379–9387; doi:10.1021/jo802165k

data_4023916
_publ_section_title
;
 Concise Stereocontrolled Formal Synthesis of (\+-)-Quinine and
 Total Synthesis of (\+-)-7- Hydroxyquinine via Merged
 Morita--Baylis--Hillman--Tsuji--Trost Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9379
_journal_page_last               9387
_journal_paper_doi               10.1021/jo802165k
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C22 H27 N O6'
_chemical_formula_weight         401.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.265(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.9886(9)
_cell_length_b                   11.8356(7)
_cell_length_c                   35.078(3)
_cell_measurement_temperature    153(2)
_cell_volume                     4976.1(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.859
_diffrn_measured_fraction_theta_max 0.859
_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  0.1575
_diffrn_reflns_av_sigmaI/netI    0.4834
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            11319
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9770
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00145(18)
_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   0.888
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         7514
_refine_ls_number_restraints     390
_refine_ls_restrained_S_all      0.888
_refine_ls_R_factor_all          0.3545
_refine_ls_R_factor_gt           0.0724
_refine_ls_shift/su_max          1.386
_refine_ls_shift/su_mean         0.059
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                1879
_reflns_number_total             7514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802165k_si_003.cif
_cod_data_source_block           paw56
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023916