Syntheses of (+)-30-epi-, (-)-6-epi-, (±)-6,30-epi-13,14-Didehydroxyisogarcinol and (±)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective, Lewis Acid-Controlled Cyclizations.
Boyce, Jonathan H.; Eschenbrenner-Lux, Vincent; Porco, Jr, John A; Journal of the American Chemical Society 138 (2016) 14789–14797; doi:10.1021/jacs.6b09727

data_4125296
_publ_section_title
;
 Syntheses of (+)-30-epi-, (-)-6-epi-,
 (+-)-6,30-epi-13,14-Didehydroxyisogarcinol and
 (+-)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective,
 Lewis Acid-Controlled Cyclizations.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14789
_journal_page_last               14797
_journal_paper_doi               10.1021/jacs.6b09727
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C32 H38 O4'
_chemical_formula_sum            'C32 H38 O4'
_chemical_formula_weight         486.62
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-30 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.1187(4)
_cell_length_b                   7.8379(2)
_cell_length_c                   15.2175(3)
_cell_measurement_reflns_used    9398
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.529
_cell_measurement_theta_min      3.824
_cell_volume                     2757.44(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Proteum-R'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  Montel
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            71181
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.700
_diffrn_reflns_theta_max         66.700
_diffrn_reflns_theta_min         3.824
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.7926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.192
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4823
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0390P)^2^+0.6910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0772
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4762
_reflns_number_total             4823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09727_si_004.cif
_cod_data_source_block           boyce5_orh
_cod_depositor_comments
'Adding full bibliography for 4125295--4125297.cif.'
_cod_database_code               4125296
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              19438
_shelx_hkl_checksum              50065