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_4129626
_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         'C25 H27 F O3'
_chemical_formula_sum            'C25 H27 F O3'
_chemical_formula_weight         394.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-09
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                78.356(5)
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_cell_formula_units_Z            2
_cell_length_a                   8.2096(4)
_cell_length_b                   10.3606(6)
_cell_length_c                   12.5374(7)
_cell_measurement_reflns_used    3289
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.5460
_cell_measurement_theta_min      4.1360
_cell_volume                     1022.58(10)
_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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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'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -11.00   83.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -       15.7256   77.0000 -120.0000 94

  2 omega  -11.00   83.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -       15.7256   77.0000   90.0000 94

  3 omega  -52.00   42.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -       15.7256  -77.0000  120.0000 94

  4 omega  -52.00   32.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -       15.7256  -57.0000    0.0000 84

  5 omega  -43.00   51.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      -16.6631   77.0000  -30.0000 94

  6 omega   34.00   88.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -       15.7256 -178.0000  -30.0000 54

  7 omega  -84.00    0.00   1.0000   11.2800
omega____ theta____ kappa____ phi______ frames
    -      -16.6631  -57.0000  -30.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
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_diffrn_orient_matrix_UB_11      -0.0378946000
_diffrn_orient_matrix_UB_12      -0.0550678000
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_diffrn_orient_matrix_UB_21      0.0508003000
_diffrn_orient_matrix_UB_22      -0.0128776000
_diffrn_orient_matrix_UB_23      0.0463588000
_diffrn_orient_matrix_UB_31      -0.0614055000
_diffrn_orient_matrix_UB_32      0.0433871000
_diffrn_orient_matrix_UB_33      0.0251727000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11090
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.544
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76259
_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.
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_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description
;
;
_exptl_crystal_F_000             420
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_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.173
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0539P)^2^+0.1485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2872
_reflns_number_total             3584
_reflns_threshold_expression     'I > 2\s(I)'
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_cod_data_source_block           liubo-zhufbyq
_cod_original_cell_volume        1022.59(10)
_cod_database_code               4129626
_reflns_odcompleteness_completeness 99.71
_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:
 C006(H006), C00E(H00E), C00H(H00H)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00N(H00C,H00F), C00O(H00G,H00M), C00P(H00N,H00O)
2.c Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00S(H00V)
2.d Idealised Me refined as rotating group:
 C00Q(H00P,H00Q,H00R), C00R(H00S,H00T,H00U), C00T(H00W,H00X,H00Y)
2.e Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_shelx_res_checksum              32125
_shelx_hkl_checksum              64242
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'