Total Synthesis of (+)-Cassaine via Transannular Diels-Alder Reaction
Serge Phoenix; Maddi Sridhar Reddy; Pierre Deslongchamps; Journal of the American Chemical Society 130 (2008) 13989–13995; doi:10.1021/ja805097s

data_4108513
_publ_section_title
;
 Total Synthesis of (+)-Cassaine via Transannular Diels-Alder Reaction
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13989
_journal_page_last               13995
_journal_paper_doi               10.1021/ja805097s
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C22 H33 F3 O6 S'
_chemical_formula_weight         482.54
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5849(10)
_cell_length_b                   12.3370(11)
_cell_length_c                   16.4652(15)
_cell_measurement_temperature    198(2)
_cell_volume                     2353.3(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_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      198(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16326
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       Parallelepip
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.6
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0548P)^2^+0.1261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                4754
_reflns_number_total             5243
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja805097s_si_002.cif
_cod_data_source_block           pd
_cod_database_code               4108513