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_4129634
_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 H39 N O7'
_chemical_formula_sum            'C34 H39 N O7'
_chemical_formula_weight         573.66
_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             2015-02-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.438(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7541(7)
_cell_length_b                   36.2871(18)
_cell_length_c                   7.3993(5)
_cell_measurement_reflns_used    1570
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.7940
_cell_measurement_theta_min      4.0010
_cell_volume                     3027.0(3)
_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
;
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 0.990
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
'#__ type_ start__ end____ width___ exp.time_ 1 omega -11.00 83.00 0.5000 11.8600 omega____ theta____ kappa____ phi______ frames - 15.5694 77.0000 30.0000 188'
_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      0.0563042000
_diffrn_orient_matrix_UB_12      -0.0082210000
_diffrn_orient_matrix_UB_13      0.0142790000
_diffrn_orient_matrix_UB_21      0.0117867000
_diffrn_orient_matrix_UB_22      0.0023964000
_diffrn_orient_matrix_UB_23      0.0983686000
_diffrn_orient_matrix_UB_31      -0.0253317000
_diffrn_orient_matrix_UB_32      -0.0175253000
_diffrn_orient_matrix_UB_33      0.0066282000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            18414
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.369
_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  0.75045
_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    1.259
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         6123
_refine_ls_number_restraints     948
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0761
_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^)+(0.0840P)^2^+1.6620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1884
_refine_ls_wR_factor_ref         0.2105
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4116
_reflns_number_total             6123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b08958_si_012.cif
_cod_data_source_block           liubo-slq-byx-no2
_cod_database_code               4129634
_reflns_odcompleteness_completeness 74.76
_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. Uiso/Uaniso restraints and constraints
C006 \\sim C007 \\sim C008 \\sim C009 \\sim C00A \\sim C00B \\sim C00C \\sim
C00F \\sim C00G \\sim C00H \\sim C00I \\sim C00J \\sim C00K \\sim C00L \\sim
C00M \\sim C00N \\sim C00O \\sim C00P \\sim C00R \\sim C00S \\sim C00T \\sim
C00U \\sim C00V \\sim C00W \\sim C00X \\sim C00Y \\sim C00Z \\sim C010 \\sim
C011 \\sim C012 \\sim C013 \\sim C014 \\sim C015 \\sim C016: within 3.8A with
sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C007(H007), C009(H009), C00L(H00L), C00P(H00P)
3.b Secondary CH2 refined with riding coordinates:
 C00G(H00B,H00C), C00I(H00D,H00E), C00Z(H00G,H00H), C010(H01A,H01B), C016(H01R,
 H01S)
3.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F), C00N(H00N), C00O(H00O), C00R(H00R), C00T(H00T),
 C00U(H00U), C00V(H00V), C00X(H00X), C00Y(H00Y)
3.d Idealised Me refined as rotating group:
 C011(H01C,H01D,H01E), C012(H01F,H01G,H01H), C013(H01I,H01J,H01K), C014(H01L,
 H01M,H01N), C015(H01O,H01P,H01Q)
;
_shelx_res_checksum              6795
_shelx_hkl_checksum              11162
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'