Total synthesis of (<i>ent</i>)-linderolide E and (<i>ent</i>)-15-hydroxy- and 15-acetoxyisogermafurenolides, and structural revision of (<i>ent</i>)-linderolide E.
Suresh, Anisha; Shingole, Mahendra; Kaliappan, Krishna P.; Organic & biomolecular chemistry 24 (2026) 1678–1682; doi:10.1039/d6ob00001k

data_7160960
_publ_section_title
;
 Total synthesis of (<i>ent</i>)-linderolide E and
 (<i>ent</i>)-15-hydroxy- and 15-acetoxyisogermafurenolides, and
 structural revision of (<i>ent</i>)-linderolide E.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1678
_journal_page_last               1682
_journal_paper_doi               10.1039/d6ob00001k
_journal_volume                  24
_journal_year                    2026
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H23 Br O4'
_chemical_formula_sum            'C22 H23 Br O4'
_chemical_formula_weight         431.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-03-24
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-08-23 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3798(15)
_cell_length_b                   10.7769(19)
_cell_length_c                   19.553(3)
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      22.26
_cell_measurement_theta_min      2.41
_cell_volume                     1976.5(6)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14108
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.083
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4424
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1414 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.5933.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.094(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0326P)^2^+0.4216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2789
_reflns_number_total             3477
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00001k2.cif
_cod_data_source_block           kpk_227_as_112_0m
_cod_depositor_comments
'Adding full bibliography for 7160958--7160961.cif.'
_cod_database_code               7160960
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.632
_shelx_estimated_absorpt_t_min   0.472
_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
2.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C13(H13), C14(H14), C20(H20)
2.d X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              92990
_olex2_submission_special_instructions 'No special instructions were received'