Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type Cyclization: Total Synthesis of Akaol A.
Kakde, Badrinath N.; Kumar, Nivesh; Mondal, Pradip Kumar; Bisai, Alakesh; Organic letters 18 (2016) 1752–1755; doi:10.1021/acs.orglett.6b00446

data_1555506
_publ_section_title
;
 Approach to Merosesquiterpenes via Lewis Acid Catalyzed Nazarov-Type
 Cyclization: Total Synthesis of Akaol A.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1752
_journal_page_last               1755
_journal_paper_doi               10.1021/acs.orglett.6b00446
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_sum            'C26 H36 O3'
_chemical_formula_weight         396.54
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.986(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2913(7)
_cell_length_b                   7.9908(4)
_cell_length_c                   13.7239(9)
_cell_measurement_reflns_used    3195
_cell_measurement_temperature    243(2)
_cell_measurement_theta_max      27.02
_cell_measurement_theta_min      2.33
_cell_volume                     1117.65(12)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      243(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.983
_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  0.0318
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9125
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         2.659
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       Plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1221 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5201
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0666
_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^)+(0.0656P)^2^+0.4252P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                3623
_reflns_number_total             5201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00446_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C13 H18 O1.50'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     198.27
_cod_database_code               1555506
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              8678
_shelx_hkl_checksum              28084