Concise syntheses of (-)-habiterpenol and (+)-2,3-<i>epi</i>-habiterpenol <i>via</i> redox radical cyclization of alkenylsilane.
Taguchi, Haruki; Kawaguchi, Mayuko; Nagamitsu, Tohru; Ohtawa, Masaki; Organic & biomolecular chemistry 21 (2023) 6129–6133; doi:10.1039/d3ob01062g

data_7159479
_publ_section_title
;
 Concise syntheses of (-)-habiterpenol and (+)-2,3-<i>epi</i>-habiterpenol
 <i>via</i> redox radical cyclization of alkenylsilane.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6129
_journal_page_last               6133
_journal_paper_doi               10.1039/d3ob01062g
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C27 H40 O'
_chemical_formula_sum            'C27 H40 O'
_chemical_formula_weight         380.61
_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     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-04-21 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.239(8)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   13.3948(3)
_cell_length_b                   6.52070(14)
_cell_length_c                   13.5565(3)
_cell_measurement_reflns_used    9745
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.20
_cell_measurement_theta_min      3.50
_cell_volume                     1103.65(7)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12436
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.198
_diffrn_reflns_theta_min         3.498
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             420.00
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.23
_refine_ls_abs_structure_details
;
 Flack x determined using 807 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3832
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0633P)^2^+0.4368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.892
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                2859
_reflns_number_total             3832
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            d3ob01062g2.cif
_cod_data_source_block           taguchi20211203-1
_cod_depositor_comments
'Adding full bibliography for 7159478--7159480.cif.'
_cod_database_code               7159479
_shelx_res_checksum              2152