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_7160959
_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         '2(C22 H23 Br O4)'
_chemical_formula_sum            'C44 H46 Br2 O8'
_chemical_formula_weight         862.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-11-21
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.884(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2933(3)
_cell_length_b                   14.1291(5)
_cell_length_c                   19.7449(6)
_cell_measurement_reflns_used    4276
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      20.4620
_cell_measurement_theta_min      1.7720
_cell_volume                     2023.95(13)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -127.56  18.44   2.00    3.00    --  -22.85 -59.25  20.08   73
  2  \w   -127.56  18.44   2.00    3.00    --  -22.85 -59.25-135.92   73
  3  \w   -127.56  18.44   2.00    3.00    --  -22.85 -59.25 122.08   73
  4  \w   -127.56  18.44   2.00    3.00    --  -22.85 -59.25 -33.92   73
  5  \w   -127.56  18.44   2.00    3.00    --  -22.85 -59.25 173.08   73
  6  \w   -115.56  18.44   2.00    3.00    --  -22.85 -59.25 -84.92   67
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0312391000
_diffrn_orient_matrix_UB_12      0.0128275000
_diffrn_orient_matrix_UB_13      0.0315970000
_diffrn_orient_matrix_UB_21      0.0132873000
_diffrn_orient_matrix_UB_22      0.0484396000
_diffrn_orient_matrix_UB_23      -0.0074831000
_diffrn_orient_matrix_UB_31      -0.0917241000
_diffrn_orient_matrix_UB_32      0.0026798000
_diffrn_orient_matrix_UB_33      -0.0158142000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.775
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.085
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(8)
_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     491
_refine_ls_number_reflns         7130
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.444
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0591
_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^)+(0.0567P)^2^+0.0640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4400
_reflns_number_total             7130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00001k2.cif
_cod_data_source_block           kpk_227_as_115_autored
_cod_depositor_comments
'Adding full bibliography for 7160958--7160961.cif.'
_cod_database_code               7160959
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.845
_shelx_estimated_absorpt_t_min   0.684
_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. Uiso/Uaniso restraints and constraints
Uanis(Br02) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
3.a Ternary CH refined with riding coordinates:
 C00E(H00G), C00L(H00L), C00N(H00N), C00Z(H00Z)
3.b Secondary CH2 refined with riding coordinates:
 C00F(H00H,H00I), C00S(H00P,H00Q), C00X(H00C,H00D), C00Y(H00E,H00F), C013(H01O,
 H01P), C01E(H01I,H01J)
3.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00U(H00U), C015(H015), C016(H016), C019(H019), C01A(H01D),
 C01C(H01E), C01F(H01K), C01G(H01T), C01H(H01L)
3.d X=CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00T(H00R,H00S), C012(H01M,H01N), C1(H1A,H1B)
3.e Idealised Me refined as rotating group:
 C00P(H00K,H00M,H00O), C017(H01A,H01B,H01C), C018(H01Q,H01R,H01S), C01D(H01F,
 H01G,H01H)
;
_shelx_res_checksum              78429
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.482
_oxdiff_exptl_absorpt_empirical_full_min 0.478