Intramolecular Diels-Alder/Tsuji allylation assembly of the functionalized trans-decalin of salvinorin A.
Burns, Aaron C.; Forsyth, Craig J.; Organic letters 10 (2008) 97–100; doi:10.1021/ol7024058

data_1504472
_publ_section_title
;
 Intramolecular Diels-Alder/Tsuji allylation assembly of the
 functionalized trans-decalin of salvinorin A.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              97
_journal_page_last               100
_journal_paper_doi               10.1021/ol7024058
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H26 O4'
_chemical_formula_weight         306.39
_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                   10.4487(14)
_cell_length_b                   10.7250(15)
_cell_length_c                   15.021(2)
_cell_measurement_reflns_used    3023
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.33
_cell_volume                     1683.3(4)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'SHELXTL, Bruker'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART Platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14080
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.894777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
'Flack H D (1983), 1643 Friedel Pairs, Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0797P)^2^+0.4128P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1355
_reflns_number_gt                2060
_reflns_number_total             2202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7024058-file003.cif
_cod_data_source_block           06232final
_cod_original_cell_volume        1683.2(4)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1504472