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_4129638
_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         'C21 H36 O5'
_chemical_formula_sum            'C21 H36 O5'
_chemical_formula_weight         368.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-25
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.7035(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.6962(2)
_cell_length_b                   9.17775(13)
_cell_length_c                   22.1774(3)
_cell_measurement_reflns_used    7082
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.7790
_cell_measurement_theta_min      3.9860
_cell_volume                     4007.17(9)
_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)
;
_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, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -88.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  125.0000   30.0000 86

  2 omega  -33.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -57.0000  -60.0000 87

  3 omega    7.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   77.0000 -180.0000 98

  4 omega    7.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   77.0000   60.0000 98

  5 omega    1.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -99.0000 -180.0000 75

  6 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486 -125.0000  120.0000 67

  7 omega   13.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   38.0000    0.0000 93

  8 omega  -33.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486  -57.0000  -30.0000 87

  9 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486 -125.0000  -60.0000 67

 10 omega   13.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.5486   38.0000  150.0000 93

 11 omega   37.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 54

 12 omega   37.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 54

 13 omega   37.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 54

 14 omega   38.00   98.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 60

 15 omega   37.00   91.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 54

 16 omega   37.00  115.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

 17 omega   88.00  161.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 73

 18 omega  116.00  165.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   60.0000 49

 19 omega   39.00  136.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 97
;
_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      0.0611961000
_diffrn_orient_matrix_UB_12      -0.0035676000
_diffrn_orient_matrix_UB_13      0.0448651000
_diffrn_orient_matrix_UB_21      -0.0276059000
_diffrn_orient_matrix_UB_22      0.1356564000
_diffrn_orient_matrix_UB_23      0.0320025000
_diffrn_orient_matrix_UB_31      -0.0401733000
_diffrn_orient_matrix_UB_32      -0.0988631000
_diffrn_orient_matrix_UB_33      0.0423344000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21592
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         3.988
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
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    1.222
_exptl_crystal_description       plate
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.547
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_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     485
_refine_ls_number_reflns         7152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0684
_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^)+(0.1318P)^2^+0.4874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1866
_refine_ls_wR_factor_ref         0.2045
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5499
_reflns_number_total             7152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08958_si_003.cif
_cod_data_source_block           slq11087
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C21 H36 O5)'
_cod_original_formula_sum        'C42 H72 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     736.99
_cod_database_code               4129638
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C00C(H00C), C00E(H00E), C00G(H00R), C00N(H00U), C00U(H00Z), C00X(H00X),
 C00Y(H00Y), C010(H010)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00A,H00B), C00F(H00P,H00Q), C00L(H00D,H00F), C00M(H00S,H00T), C00O(H00G,
 H00H), C00P(H00V,H00W), C00T(H00I,H00J), C00V(H00K,H00L), C012(H01Q,H01R),
 C015(H01V,H01W), C017(H01X,H01Y), C019(H01G,H01H), C01B(H0AA,HD), C01C(H01I,
 H01J)
2.c Idealised Me refined as rotating group:
 C00W(H00M,H00N,H00O), C013(H01A,H01B,H01C), C014(H01S,H01T,H01U), C016(H01D,
 H01E,H01F), C018(H01Z,H,HA), C01A(H01,HB,HC), C01D(H1AA,HE,HF), C01E(H2AA,HG,
 HH), C01F(H01K,H01L,H01M), C01G(H01N,H01O,H01P)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003), O004(H004), O006(H006), O007(H007)
;
_shelx_res_checksum              44919
_shelx_hkl_checksum              89853
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'