Total Synthesis of Atisane-Type Diterpenoids: Application of Diels-Alder Cycloadditions of Podocarpane-Type Unmasked ortho-Benzoquinones.
Song, Liqiang; Zhu, Guili; Liu, Yongjiang; Liu, Bo; Qin, Song; Journal of the American Chemical Society 137 (2015) 13706–13714; doi:10.1021/jacs.5b08958

data_4129633
_publ_section_title
;
 Total Synthesis of Atisane-Type Diterpenoids: Application of Diels-Alder
 Cycloadditions of Podocarpane-Type Unmasked ortho-Benzoquinones.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13706
_journal_page_last               13714
_journal_paper_doi               10.1021/jacs.5b08958
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C34 H38 F N O7'
_chemical_formula_sum            'C34 H38 F N O7'
_chemical_formula_weight         591.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-10
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                104.911(6)
_cell_angle_beta                 91.060(6)
_cell_angle_gamma                90.150(6)
_cell_formula_units_Z            2
_cell_length_a                   7.3015(6)
_cell_length_b                   11.9676(8)
_cell_length_c                   18.1605(11)
_cell_measurement_reflns_used    4685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7550
_cell_measurement_theta_min      3.7640
_cell_volume                     1533.15(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -52.00   42.00   1.0000   23.0900
omega____ theta____ kappa____ phi______ frames
    -       15.5694  -77.0000 -180.0000 94

  2 omega  -54.00   85.00   1.0000   23.0900
omega____ theta____ kappa____ phi______ frames
    -       15.5694    0.0000   90.0000 139

  3 omega   -1.00   83.00   1.0000   23.0900
omega____ theta____ kappa____ phi______ frames
    -       15.5694   57.0000  -60.0000 84

  4 omega  -84.00   10.00   1.0000   23.0900
omega____ theta____ kappa____ phi______ frames
    -      -16.6631  -77.0000   60.0000 94

  5 omega  -71.00  -25.00   1.0000   23.0900
omega____ theta____ kappa____ phi______ frames
    -      -16.6631  127.0000  -90.0000 46

  6 omega   35.00   88.00   1.0000   23.0900
omega____ theta____ kappa____ phi______ frames
    -       15.5694  178.0000  150.0000 53

  7 omega   -3.00   85.00   1.0000   23.0900
omega____ theta____ kappa____ phi______ frames
    -       15.5694   38.0000 -150.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0346647000
_diffrn_orient_matrix_UB_12      0.0313200000
_diffrn_orient_matrix_UB_13      -0.0250540000
_diffrn_orient_matrix_UB_21      -0.0261661000
_diffrn_orient_matrix_UB_22      -0.0459878000
_diffrn_orient_matrix_UB_23      -0.0316981000
_diffrn_orient_matrix_UB_31      -0.0869165000
_diffrn_orient_matrix_UB_32      0.0258117000
_diffrn_orient_matrix_UB_33      -0.0013465000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16682
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.337
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74032
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description
;
;
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0837P)^2^+0.4788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3929
_reflns_number_total             5405
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08958_si_014.cif
_cod_data_source_block           liubo-zhufnobyx
_cod_database_code               4129633
_reflns_odcompleteness_completeness 99.79
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_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C00Y, C017
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3.a Ternary CH refined with riding coordinates:
 C008(H008), C00F(H00F), C00G(H00G), C00K(H00K)
3.b Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00C), C00L(H00D,H00E), C00T(H00I,H00L), C00W(H00M,H00N), C00Z(H00P,
 H00Q)
3.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00H(H00H), C00J(H00J), C00O(H00O), C00S(H00S), C00U(H00U),
 C010(H010), C014(H014), C017(H017)
3.d Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C), C012(H01D,H01E,H01F), C013(H01G,H01H,H01I), C015(H01J,
 H01K,H01L), C016(H01M,H01N,H01O)
;
_shelx_res_checksum              9239
_shelx_hkl_checksum              69536
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'