Development of a Unified Enantioselective, Convergent Synthetic Approach Toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes: Asymmetric Formation of the Polycyclic Norditerpenoid Carbocyclic Core by Tandem Annulation Cascade.
Craig, 2nd, Robert A; Smith, Russell C.; Roizen, Jennifer L.; Jones, Amanda C.; Virgil, Scott C.; Stoltz, Brian M.; The Journal of organic chemistry 83 (2018) 3467–3485; doi:10.1021/acs.joc.7b02825

data_4035486
_publ_section_title
;
 Development of a Unified Enantioselective, Convergent Synthetic Approach
 Toward the Furanobutenolide-Derived Polycyclic Norcembranoid Diterpenes:
 Asymmetric Formation of the Polycyclic Norditerpenoid Carbocyclic Core by
 Tandem Annulation Cascade.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3467
_journal_page_last               3485
_journal_paper_doi               10.1021/acs.joc.7b02825
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H22 O5'
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370),
 SHELXL-2017/1,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 107.751(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.5468(19)
_cell_length_b                   10.4722(9)
_cell_length_c                   7.3277(5)
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.06
_cell_measurement_theta_min      4.70
_cell_volume                     1647.8(2)
_computing_cell_refinement       'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'BIS V6.2.1/2016-03-01'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19495
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         79.209
_diffrn_reflns_theta_min         4.698
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.787
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1158 before and 0.0600 after correction. The Ratio
of minimum to maximum transmission is 0.8733. The \l/2 correction
factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0387P)^2^+0.5302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0699
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3498
_reflns_number_total             3531
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02825_si_009.cif
_cod_data_source_block           p17139
_cod_database_code               4035486
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.787
_refine_ls_abs_structure_hooft   0.08(4)
_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. Others
 Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18A)=Sof(H18C)=Sof(H18D)=1-FVAR(1)
 Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C11(H11), C14(H14), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B), C9(H9A,H9B), C13(H13A,H13B)
3.c X=CH2 refined with riding coordinates:
 C18(H18A,H18B), C18A(H18C,H18D)
3.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C17A(H17D,H17E,H17F), C19(H19A,H19B,H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              77479
_shelx_hkl_checksum              9413
_olex2_submission_special_instructions 'No special instructions were received'