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_4129630
_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         'C35 H41 N O8'
_chemical_formula_sum            'C35 H41 N O8'
_chemical_formula_weight         603.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-11
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Olex2 1.2
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_cell_measurement_reflns_used    4932
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.9990
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_computing_cell_refinement
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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_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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
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_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -20.00   55.00   1.0000   22.9950
omega____ theta____ kappa____ phi______ frames
    -       15.5694  -99.0000   90.0000 75

  2 omega  -20.00   55.00   1.0000   22.9950
omega____ theta____ kappa____ phi______ frames
    -       15.5694  -99.0000    0.0000 75

  3 omega   -3.00   85.00   1.0000   22.9950
omega____ theta____ kappa____ phi______ frames
    -       15.5694   38.0000  -60.0000 88

  4 omega  -52.00   29.00   1.0000   22.9950
omega____ theta____ kappa____ phi______ frames
    -       15.5694  -57.0000  150.0000 81
;
_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      -0.0038749000
_diffrn_orient_matrix_UB_12      -0.0192364000
_diffrn_orient_matrix_UB_13      -0.0285379000
_diffrn_orient_matrix_UB_21      -0.0356479000
_diffrn_orient_matrix_UB_22      -0.0397776000
_diffrn_orient_matrix_UB_23      -0.0039817000
_diffrn_orient_matrix_UB_31      -0.0166545000
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_diffrn_orient_matrix_UB_33      -0.0078939000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19762
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.339
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71756
_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    1.253
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_parameters     403
_refine_ls_number_reflns         6529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0559
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0564P)^2^+0.1562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3894
_reflns_number_total             6529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08958_si_013.cif
_cod_data_source_block           zhumonobyx
_cod_database_code               4129630
_reflns_odcompleteness_completeness 99.55
_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
2.a Ternary CH refined with riding coordinates:
 C00A(H00C), C00F(H00F), C00I(H00I), C00N(H00N)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00H(H00E,H00G), C00J(H00H,H00J), C00O(H00K,H00L), C00S(H00R,
 H00S)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00M(H00M), C00T(H00T), C00V(H00X), C00Y(H00Z), C010(H010),
 C015(H015), C016(H016), C017(H017)
2.d Idealised Me refined as rotating group:
 C00P(H00O,H00P,H00Q), C00U(H00U,H00V,H00W), C00X(H00Y,H,HA), C012(H01A,H01B,
 H01C), C014(H01D,H01E,H01F), C018(H01G,H01H,H01I)
;
_shelx_res_checksum              16107
_shelx_hkl_checksum              5824
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'