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_4129631
_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         'C20 H34 O2'
_chemical_formula_sum            'C20 H34 O2'
_chemical_formula_weight         306.47
_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             2014-12-31
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Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4973)
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_cell_angle_alpha                90
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_cell_length_b                   20.5798(3)
_cell_length_c                   9.20240(15)
_cell_measurement_reflns_used    3742
_cell_measurement_temperature    126(9)
_cell_measurement_theta_max      72.5200
_cell_measurement_theta_min      4.2960
_cell_volume                     1791.27(5)
_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_environment      N~2~
_diffrn_ambient_temperature      126(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details
;
  1 omega  -35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -19.0000  150.0000 101

  2 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000    0.0000 84

  3 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000  120.0000 94

  4 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -90.0000 74

  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -30.0000 74

  6 omega   39.00  109.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 70

  7 omega   38.00   91.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

  8 omega   38.00   91.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

  9 omega   81.00  176.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

 10 omega   40.00   98.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 11 omega   38.00   91.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 53

 12 omega   38.00   91.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 13 omega   39.00   89.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 50
;
_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      0.0643215000
_diffrn_orient_matrix_UB_12      0.0674704000
_diffrn_orient_matrix_UB_13      -0.0209531000
_diffrn_orient_matrix_UB_21      0.0590295000
_diffrn_orient_matrix_UB_22      -0.0249219000
_diffrn_orient_matrix_UB_23      -0.1372974000
_diffrn_orient_matrix_UB_31      -0.1374255000
_diffrn_orient_matrix_UB_32      0.0209068000
_diffrn_orient_matrix_UB_33      -0.0962400000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7593
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.691
_diffrn_reflns_theta_min         4.297
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90242
_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.
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_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    1.136
_exptl_crystal_description
;
;
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     205
_refine_ls_number_reflns         3326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0591
_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^)+(0.1040P)^2^+0.3250P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1485
_refine_ls_wR_factor_ref         0.1558
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2952
_reflns_number_total             3326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08958_si_004.cif
_cod_data_source_block           lb-slq11132-2
_cod_original_cell_volume        1791.28(5)
_cod_database_code               4129631
_reflns_odcompleteness_completeness 96.58
_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:
 C003(H003), C004(H004), C00D(H00I), C00F(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C006(H00A,H00B), C007(H00C,H00D), C00B(H00E,H00F), C00C(H00G,H00H), C00E(H00J,
 H00K), C00H(H00P,H00Q), C00I(H00R,H00S), C00J(H00T,H00U)
2.c Idealised Me refined as rotating group:
 C00G(H00M,H00N,H00O), C00K(H00V,H00W,H00X), C00L(H00Y,H,HA), C00M(H00Z,HB,HC)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002)
;
_shelx_res_checksum              89358
_shelx_hkl_checksum              82116
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2014-12-31
_olex2_submission_special_instructions 'No special instructions were received'