An IMDAF Cycloaddition Approach toward the Synthesis of the Lycopodium Alkaloid (\±)-Fawcettidine
Jutatip Boonsompat; Albert Padwa; Journal of Organic Chemistry 76 (2011) 2753–2761; doi:10.1021/jo200125c

data_4026218
_publ_section_title
;
 An IMDAF Cycloaddition Approach toward the Synthesis of the Lycopodium
 Alkaloid (\+-)-Fawcettidine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2753
_journal_page_last               2761
_journal_paper_doi               10.1021/jo200125c
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C23 H35 N O6 Si'
_chemical_formula_sum            'C23 H35 N O6 Si'
_chemical_formula_weight         449.61
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.534(3)
_cell_angle_beta                 90.775(3)
_cell_angle_gamma                109.493(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4494(3)
_cell_length_b                   12.0453(5)
_cell_length_c                   14.0749(8)
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      59.548
_cell_measurement_theta_min      8.299
_cell_volume                     1208.98(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.745
_diffrn_measured_fraction_theta_max 0.745
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5231
_diffrn_reflns_theta_full        60.35
_diffrn_reflns_theta_max         60.35
_diffrn_reflns_theta_min         8.30
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.168
_exptl_absorpt_correction_T_max  0.9332
_exptl_absorpt_correction_T_min  0.6337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0500P)^2^+0.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                2231
_reflns_number_total             2695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200125c_si_002.cif
_cod_data_source_block           fawdas
_cod_database_code               4026218