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_7160961
_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         'C14 H20 O3'
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30
_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             2022-02-14
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.910(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8535(2)
_cell_length_b                   8.0124(2)
_cell_length_c                   9.0131(2)
_cell_measurement_reflns_used    5434
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.5850
_cell_measurement_theta_min      2.3250
_cell_volume                     617.84(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f   -169.73  14.27   1.00    2.00   9.41 -12.98 -31.50    --   184
  2  \f     24.08 208.08   1.00    2.00  16.12 -12.98 -59.25    --   184
  3  \w   -108.63  15.37   1.00    2.00    --  -12.98 -59.25  71.08  124
  4  \w   -108.63  15.37   1.00    2.00    --  -12.98 -59.25 -33.92  124
  5  \w   -108.63  15.37   1.00    2.00    --  -12.98 -59.25  20.08  124
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0648308000
_diffrn_orient_matrix_UB_12      0.0017394000
_diffrn_orient_matrix_UB_13      0.0326194000
_diffrn_orient_matrix_UB_21      -0.0394451000
_diffrn_orient_matrix_UB_22      0.0554491000
_diffrn_orient_matrix_UB_23      -0.0585289000
_diffrn_orient_matrix_UB_31      -0.0333621000
_diffrn_orient_matrix_UB_32      -0.0689971000
_diffrn_orient_matrix_UB_33      -0.0462975000
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16706
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.462
_diffrn_reflns_theta_min         2.338
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         4063
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0454P)^2^+0.0015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                3307
_reflns_number_total             4063
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00001k2.cif
_cod_data_source_block           kpk_170_as_169_autored
_cod_depositor_comments
'Adding full bibliography for 7160958--7160961.cif.'
_cod_database_code               7160961
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.979
_reflns_odcompleteness_completeness 89.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.39
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              62596
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.858