Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin
Tarek Sammakia; Deidre M. Johns; Ganghyeok Kim; Martin A. Berliner; Journal of the American Chemical Society 127 (2005) 6504–6505; doi:10.1021/ja043506g

data_4111681
_publ_section_title
;
 Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder
 Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6504
_journal_page_last               6505
_journal_paper_doi               10.1021/ja043506g
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C16 H26 O3'
_chemical_formula_weight         266.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.83(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.521(3)
_cell_length_b                   7.874(4)
_cell_length_c                   18.048(8)
_cell_measurement_reflns_used    1607
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      29.885
_cell_measurement_theta_min      2.826
_cell_volume                     779.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      143(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  ' Siemens SMART CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7622
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.14
_diffrn_standards_decay_%        0(1)
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4.1(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0727P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1304
_reflns_number_gt                1842
_reflns_number_total             2760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja043506gsi20041112_114411.cif
_cod_data_source_block           bc426
_cod_database_code               4111681