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_4129637
_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 H28 O3'
_chemical_formula_sum            'C25 H28 O3'
_chemical_formula_weight         376.47
_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             2014-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
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_cell_formula_units_Z            2
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_cell_length_b                   11.8729(6)
_cell_length_c                   11.9755(5)
_cell_measurement_reflns_used    5110
_cell_measurement_temperature    293
_cell_measurement_theta_max      72.5360
_cell_measurement_theta_min      3.9030
_cell_volume                     1004.15(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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000  -60.0000 94

  2 omega   18.00  106.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000  150.0000 88

  3 omega   23.00   90.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000   60.0000 67

  4 omega    1.00   75.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  150.0000 74

  5 omega   20.00  104.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000    0.0000 84

  6 omega   23.00   90.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421 -125.0000 -150.0000 67

  7 omega   20.00  104.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -60.0000 84

  8 omega  -33.00   55.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000   90.0000 88

  9 omega  -31.00   53.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000    0.0000 84

 10 omega   20.00  104.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000 -120.0000 84

 11 omega   91.00  176.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 85

 12 omega   41.00  126.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 85

 13 omega   40.00  135.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 95

 14 omega   38.00  116.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 78

 15 omega   39.00  109.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 16 omega   38.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 53

 17 omega  100.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 78

 18 omega   40.00   98.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 19 omega   38.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 20 omega   38.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 21 omega   39.00  109.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 22 omega   90.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 23 omega   37.00  146.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -180.0000 109

 24 omega   57.00  150.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 93

 25 omega   10.00  104.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  150.0000 94

 26 omega  -31.00   53.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -150.0000 84

 27 omega   10.00  104.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -120.0000 94

 28 omega   10.00  104.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000   90.0000 94

 29 omega    1.00   51.00   1.0000    1.4200
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   90.0000 50
;
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_diffrn_orient_matrix_UB_11      0.0599054000
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_diffrn_orient_matrix_UB_21      -0.1845253000
_diffrn_orient_matrix_UB_22      0.0323496000
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_diffrn_orient_matrix_UB_31      -0.0814321000
_diffrn_orient_matrix_UB_32      0.0694248000
_diffrn_orient_matrix_UB_33      0.0893305000
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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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 orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.1083P)^2^+0.1739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_cod_data_source_block           liubo-zhu-aryne
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_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:
 C00A(H00A), C00J(H00J), C00N(H00P)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00E,H00F), C00M(H00N,H00O), C00P(H00Q,H00R), C00Q(H00S,H00T)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G), C00I(H00I),
 C00K(H00K)
2.d Idealised Me refined as rotating group:
 C00L(H00H,H00L,H00M), C00R(H00U,H00V,H00W), C00S(H00X,H00Y,H)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_shelx_res_checksum              98666
_shelx_hkl_checksum              86056
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'