Enantioselective Total Synthesis of (+)-Scuteflorin A Using Organocatalytic Asymmetric Epoxidation
Christopher J. Bartlett; David P. Day; Yohan Chan; Steven M. Allin; Michael J. McKenzie; Alexandra M. Z. Slawin; Philip C. Bulman Page; Journal of Organic Chemistry 77 (2012) 772–774; doi:10.1021/jo2021407

data_4026868
_publ_section_title
;
 Enantioselective Total Synthesis of (+)-Scuteflorin A Using
 Organocatalytic Asymmetric Epoxidation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              772
_journal_page_last               774
_journal_paper_doi               10.1021/jo2021407
_journal_volume                  77
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H18 O5'
_chemical_formula_sum            'C17 H18 O5'
_chemical_formula_weight         302.31
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 90.93(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.18(3)
_cell_length_b                   5.353(6)
_cell_length_c                   12.036(13)
_cell_measurement_reflns_used    2125
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.4
_cell_volume                     1493(3)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2869
_diffrn_reflns_av_sigmaI/netI    0.2439
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4642
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.9031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       Prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.123
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(5)
_refine_ls_extinction_coef       0.031(10)
_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   1.187
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.186
_refine_ls_R_factor_all          0.2189
_refine_ls_R_factor_gt           0.1817
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4014
_refine_ls_wR_factor_ref         0.4379
_reflns_number_gt                1256
_reflns_number_total             2175
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2021407_si_002.cif
_cod_data_source_block           8
_cod_database_code               4026868