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_4129635
_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_absolute_configuration rmad
_chemical_formula_moiety         'C21 H34 O6'
_chemical_formula_sum            'C21 H34 O6'
_chemical_formula_weight         382.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2011-05-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3753(4)
_cell_length_b                   13.5428(7)
_cell_length_c                   19.1838(10)
_cell_measurement_reflns_used    3279
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.3450
_cell_measurement_theta_min      3.7830
_cell_volume                     1916.12(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -20.00   55.00   1.0000   37.4300
omega____ theta____ kappa____ phi______ frames
    -       15.5694  -99.0000 -150.0000 75

  2 omega   -1.00   83.00   1.0000   37.4300
omega____ theta____ kappa____ phi______ frames
    -       15.5694   57.0000  150.0000 84

  3 omega  -27.00   19.00   1.0000   37.4300
omega____ theta____ kappa____ phi______ frames
    -      -16.5069  -93.0000 -109.0000 46

  4 omega  -33.00   51.00   1.0000   37.4300
omega____ theta____ kappa____ phi______ frames
    -      -16.5069   57.0000  -90.0000 84

  5 omega   35.00   64.00   1.0000   37.4300
omega____ theta____ kappa____ phi______ frames
    -       15.5694  178.0000  150.0000 29
;
_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      -0.0206454000
_diffrn_orient_matrix_UB_12      0.0414889000
_diffrn_orient_matrix_UB_13      0.0209726000
_diffrn_orient_matrix_UB_21      0.0281588000
_diffrn_orient_matrix_UB_22      0.0319829000
_diffrn_orient_matrix_UB_23      -0.0272487000
_diffrn_orient_matrix_UB_31      -0.0896019000
_diffrn_orient_matrix_UB_32      0.0003109000
_diffrn_orient_matrix_UB_33      -0.0135794000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12001
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         3.485
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.326
_exptl_crystal_description
;
;
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0440P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0946
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2987
_reflns_number_total             3904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08958_si_002.cif
_cod_data_source_block           liubo-slq13124
_cod_original_cell_volume        1916.11(18)
_cod_database_code               4129635
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C00J(H00L), C00K(H00M), C00N(H00R)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00D(H00C,H00D), C00G(H00E,H00F), C00I(H00J,H00K), C00L(H00N,
 H00O), C00M(H00P,H00Q)
2.c Idealised Me refined as rotating group:
 C00H(H00G,H00H,H00I), C00O(H00S,H00T,H00U), C00P(H00V,H00W,H00X), C00Q(H00Y,H,
 HA), C00R(H00Z,HB,HC)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O005(H005)
;
_shelx_res_checksum              63407
_shelx_hkl_checksum              55447
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-06-10
_olex2_submission_special_instructions 'No special instructions were received'