Intermolecular Radical Cation Diels-Alder (RCDA) Reaction of Bicyclooctadienes: Biomimetic Formal Total Synthesis of Kingianin A and Total Syntheses of Kingianins D, F, H, and J.
Lim, Hee Nam; Parker, Kathlyn A.; The Journal of organic chemistry 79 (2014) 919–; doi:10.1021/jo402082y

data_4029204
_publ_section_title
;
 Intermolecular Radical Cation Diels-Alder (RCDA) Reaction of
 Bicyclooctadienes: Biomimetic Formal Total Synthesis of Kingianin A and
 Total Syntheses of Kingianins D, F, H, and J.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              919
_journal_paper_doi               10.1021/jo402082y
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C34 H36 O6'
_chemical_formula_sum            'C34 H36 O6'
_chemical_formula_weight         540.63
_chemical_melting_point          164.5(5)
_chemical_name_common            'kingianin precursor'
_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
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_cell_angle_alpha                117.374(4)
_cell_angle_beta                 90.911(3)
_cell_angle_gamma                111.778(4)
_cell_formula_units_Z            2
_cell_length_a                   10.5387(4)
_cell_length_b                   12.2952(6)
_cell_length_c                   13.3080(5)
_cell_measurement_reflns_used    11463
_cell_measurement_temperature    295
_cell_measurement_theta_max      72.9830
_cell_measurement_theta_min      3.8300
_cell_volume                     1385.17(13)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_diffrn_ambient_temperature      295
_diffrn_detector_area_resol_mean 10.4962
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_diffrn_measured_fraction_theta_max 0.983
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;
  1 omega  -49.00   33.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947   37.0000  150.0000 82 
  
  2 omega -113.00  -29.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947  -37.0000    0.0000 84 
  
  3 omega  -95.00  -14.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947  122.0000  -97.0000 81 
  
  4 omega   -4.00   40.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -       40.1947  -99.0000  -90.0000 44 
  
  5 omega -135.00  -93.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000  -30.0000    0.0000 42 
  
  6 omega -135.00 -109.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000 -149.0000   18.0000 26 
  
  7 omega  -76.00  -50.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000  -30.0000    0.0000 26 
  
  8 omega   87.00  177.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   45.0000 -120.0000 90 
  
  9 omega   64.00   89.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  -30.0000   30.0000 25 
  
 10 omega   61.00   87.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  -94.0000   30.0000 26 
  
 11 omega  106.00  172.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  111.0000 -180.0000 66 
  
 12 omega   33.00   81.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  -30.0000  120.0000 48 
  
 13 omega   66.00   97.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  -45.0000 -180.0000 31 
  
 14 omega  101.00  148.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  111.0000  150.0000 47 
  
 15 omega   38.00  115.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167 -111.0000  120.0000 77 
  
 16 omega   52.00  135.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167 -149.0000   18.0000 83 
  
 17 omega  105.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  111.0000  120.0000 73 
  
 18 omega   91.00  170.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   45.0000  -60.0000 79 
  
 19 omega   34.00  134.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  -77.0000  120.0000 100 
  
 20 omega -114.00  -11.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947  -57.0000  150.0000 103 
  
 21 omega  -49.00   36.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947   37.0000   30.0000 85 
  
 22 omega -119.00   -7.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947  -77.0000  120.0000 112 
  
 23 omega -119.00   -7.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947  -77.0000  -90.0000 112 
  
 24 omega -136.00  -31.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000  -61.0000    0.0000 105 
  
 25 omega -140.00  -28.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000  -77.0000  -90.0000 112 
  
 26 omega -140.00  -28.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000  -77.0000   90.0000 112 
  
 27 omega -140.00  -28.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000  -77.0000 -180.0000 112 
  
 28 omega   79.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   45.0000  150.0000 99 
  
 29 omega   28.00  116.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167 -111.0000  -90.0000 88 
  
 30 omega   76.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   61.0000    0.0000 102 
  
 31 omega   72.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   77.0000   90.0000 106 
  
 32 omega   76.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   30.0000   90.0000 102 
  
 33 omega   72.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   77.0000 -120.0000 106 
  
 34 omega   72.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   77.0000 -180.0000 106 
  
 35 omega   72.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   77.0000  -60.0000 106 
  
 36 omega -116.00  -14.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947  -37.0000 -150.0000 102 
  
 37 omega -119.00   -7.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -      -40.1947  -77.0000    0.0000 112 
  
 38 omega   18.00   97.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -       40.1947 -125.0000   30.0000 79 
  
 39 omega   18.00   97.00   1.0000    2.3300 
omega____ theta____ kappa____ phi______ frames 
    -       40.1947 -125.0000 -150.0000 79 
  
 40 omega -140.00 -115.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      -61.5000  -77.0000  -30.0000 25 
  
 41 omega   72.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   77.0000  150.0000 106 
  
 42 omega   72.00  178.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167   77.0000   30.0000 106 
  
 43 omega   22.00  109.00   1.0000    9.3100 
omega____ theta____ kappa____ phi______ frames 
    -      106.1167  -94.0000  120.0000 87 
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0786317000
_diffrn_orient_matrix_UB_12      -0.0220762000
_diffrn_orient_matrix_UB_13      -0.0991373000
_diffrn_orient_matrix_UB_21      -0.1389887000
_diffrn_orient_matrix_UB_22      -0.1092176000
_diffrn_orient_matrix_UB_23      -0.0889312000
_diffrn_orient_matrix_UB_31      -0.0247900000
_diffrn_orient_matrix_UB_32      0.1091267000
_diffrn_orient_matrix_UB_33      -0.0131328000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29129
_diffrn_reflns_theta_full        73.39
_diffrn_reflns_theta_max         73.3989
_diffrn_reflns_theta_min         3.8399
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00059(8)
_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   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0362P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                4453
_reflns_number_total             5477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402082y_si_001.cif
_cod_data_source_block
;
;
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '164-165' was changed to '164.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4029204
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         C34H36O6