Asymmetric total synthesis of (+)-astellatol and (−)-astellatene
Zhao, Nan; Xie, Shengling; Tian, Peilin; Tong, Rongbiao; Ning, Chengqing; Xu, Jing; Organic Chemistry Frontiers 6 (2019) 2014–; doi:10.1039/C9QO00384C

data_1554899
_publ_section_title
;
 Asymmetric total synthesis of (+)-astellatol and (&#x2212;)-astellatene
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2014
_journal_paper_doi               10.1039/C9QO00384C
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C24 H36 O3'
_chemical_formula_sum            'C24 H36 O3'
_chemical_formula_weight         372.53
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-03-16 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9194(8)
_cell_length_b                   12.8315(12)
_cell_length_c                   18.5057(18)
_cell_measurement_reflns_used    7516
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.10
_cell_measurement_theta_min      4.96
_cell_volume                     2118.0(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11725
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.136
_diffrn_reflns_theta_min         4.193
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1266 before and 0.0739 after correction. The Ratio of minimum to maximum transmission is 0.6821. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.10(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0659
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0831P)^2^+0.7133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1672
_refine_ls_wR_factor_ref         0.1734
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                3438
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00384c2.cif
_cod_data_source_block           cu_d8v17002_0m
_cod_database_code               1554899
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.844
_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:
 C5(H5), C6(H6), C10(H10), C13(H13), C16(H16), C17(H17), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B), C12(H12A,
 H12B), C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              78097
_olex2_submission_special_instructions 'No special instructions were received'