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_4125297
_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         'C30 H36 O4'
_chemical_formula_sum            'C30 H36 O4'
_chemical_formula_weight         460.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-02 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 102.4190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.1854(2)
_cell_length_b                   19.4283(3)
_cell_length_c                   19.7516(3)
_cell_measurement_reflns_used    9698
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.490
_cell_measurement_theta_min      3.229
_cell_volume                     5316.13(14)
_computing_cell_refinement       'SAINT (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0399
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            53021
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.546
_diffrn_reflns_theta_max         66.546
_diffrn_reflns_theta_min         3.228
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.7019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_description       block
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         9331
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+2.4490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8667
_reflns_number_total             9331
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09727_si_002.cif
_cod_data_source_block           boyce4_0m
_cod_depositor_comments
'Adding full bibliography for 4125295--4125297.cif.'
_cod_database_code               4125297
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              32415
_shelx_hkl_checksum              16791