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_4129636
_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         'C21 H34 O5'
_chemical_formula_sum            'C21 H34 O5'
_chemical_formula_weight         366.48
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
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Olex2 1.2
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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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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
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;
  1 omega  -52.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -180.0000 87

  2 omega    7.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  3 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  4 omega    7.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6746   77.0000  120.0000 98

  5 omega   17.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6746   57.0000   90.0000 87

  6 omega  -33.00   54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6746  -57.0000  120.0000 87

  7 omega  -34.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   17.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6746   57.0000 -120.0000 87

  9 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6746 -125.0000    0.0000 67

 10 omega  -34.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6746  -77.0000  -60.0000 98

 11 omega   12.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.6746  -99.0000  -90.0000 26

 12 omega   52.00   88.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 36

 13 omega   84.00  167.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -120.0000 83

 14 omega   41.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 49

 15 omega  104.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 72

 16 omega   62.00  127.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 65

 17 omega   51.00  108.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 57

 18 omega   38.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 60

 19 omega   80.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 29

 20 omega   81.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 25

 21 omega   61.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 35

 22 omega   96.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 26
;
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_diffrn_orient_matrix_UB_11      0.0030333000
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_diffrn_reflns_av_unetI/netI     0.0214
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_diffrn_reflns_number            21121
_diffrn_reflns_point_group_measured_fraction_full 0.987
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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 light colourless'
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'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.5860P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C21 H34 O5)'
_cod_original_formula_sum        'C42 H68 O10'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     732.96
_cod_database_code               4129636
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.96
_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:
 C16(H16), C49(H49), C66(H66), C104(H104), C152(H152), C157(H157)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C27(H27A,H27B), C35(H35A,H35B), C40(H40A,H40B), C42(H42A,
 H42B), C43(H43A,H43B), C54(H54A,H54B), C56(H56A,H56B), C59(H59A,H59B),
 C71(H71A,H71B), C75(H75A,H75B), C79(H79A,H79B), C88(H88A,H88B), C135(H13D,H13E)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C),
 C52(H52A,H52B,H52C), C57(H57A,H57B,H57C), C97(H97A,H97B,H97C), C127(H12A,H12B,
 H12C), C134(H13A,H13B,H13C), C145(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O9(H9), O12(H12), O18(H18)
;
_shelx_res_checksum              24353
_shelx_hkl_checksum              11633
_olex2_submission_special_instructions 'No special instructions were received'