Discovery and bioinspired total syntheses of unprecedented sesquiterpenoid dimers unveiled bifurcating [4 + 2] cycloaddition and target differentiation of enantiomers.
He, Tao-Bin; Yan, Bing-Chao; Zhou, Yuan-Fei; Sang, Yue-Qian; Li, Xiao-Nian; Sun, Han-Dong; Wang, Chu; Xue, Xiao-Song; Puno, Pema-Tenzin; Chemical science 15 (2024) 1260–1270; doi:10.1039/d3sc05233h

data_1570422
_publ_section_title
;
 Discovery and bioinspired total syntheses of unprecedented
 sesquiterpenoid dimers unveiled bifurcating [4 + 2] cycloaddition and
 target differentiation of enantiomers.
;
_journal_issue                   4
_journal_name_full               'Chemical science'
_journal_page_first              1260
_journal_page_last               1270
_journal_paper_doi               10.1039/d3sc05233h
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H40 O4'
_chemical_formula_sum            'C30 H40 O4'
_chemical_formula_weight         464.62
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-10-14 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6842(2)
_cell_length_b                   15.4286(3)
_cell_length_c                   19.2929(4)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.99
_cell_measurement_theta_min      2.86
_cell_volume                     2584.96(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14778
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.407
_diffrn_reflns_theta_min         3.668
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.380
_exptl_transmission_factor_max   0.5854
_exptl_transmission_factor_min   0.3309
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1795 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0616P)^2^+1.0723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1147
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                4448
_reflns_number_total             4472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05233h2.cif
_cod_data_source_block           cu_she156_0m
_cod_depositor_comments
'Adding full bibliography for 1570418--1570425.cif.'
_cod_database_code               1570422
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.668
_shelx_estimated_absorpt_t_max   0.801
_shelx_res_checksum              77558