Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin H, (+)-agallochaol C, and (+)-16α, 17-dihydroxy-atisan-3-one.
Dethe, Dattatraya H.; Sharma, Nitin; Juyal, Sakshi; Singh, Prabhakar; Siddiqui, Salman A.; Chemical communications (Cambridge, England) 60 (2024) 7866–7869; doi:10.1039/d4cc01982b

data_7133136
_publ_section_title
;
 Enantioselective total synthesis of atisane diterpenoids: (+)-sapinsigin
 H, (+)-agallochaol C, and (+)-16&#x3b1;, 17-dihydroxy-atisan-3-one.
;
_journal_issue                   61
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7866
_journal_page_last               7869
_journal_paper_doi               10.1039/d4cc01982b
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H30 O'
_chemical_formula_sum            'C20 H30 O'
_chemical_formula_weight         286.461
_chemical_name_systematic        10auga_o_0m
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-23
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-23 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                64.982(1)
_cell_angle_beta                 80.954(1)
_cell_angle_gamma                87.690(1)
_cell_formula_units_Z            2
_cell_length_a                   6.0028(2)
_cell_length_b                   11.2789(3)
_cell_length_c                   13.1074(4)
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.65
_cell_measurement_theta_min      2.45
_cell_volume                     793.83(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9930
_diffrn_measured_fraction_theta_max 0.9932
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.9930
_diffrn_reflns_Laue_measured_fraction_max 0.9932
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17410
_diffrn_reflns_point_group_measured_fraction_full 0.9930
_diffrn_reflns_point_group_measured_fraction_max 0.9932
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         1.99
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2525
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1361 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.3386.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             316.160
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method Hexane
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.3847
_refine_diff_density_min         -0.1950
_refine_diff_density_rms         0.0442
_refine_ls_d_res_high            0.7471
_refine_ls_d_res_low             10.2163
_refine_ls_goodness_of_fit_ref   1.0530
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0530
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.3036P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -7
_reflns_limit_k_max              15
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                3632
_reflns_number_total             3957
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4cc01982b2.cif
_cod_data_source_block           10auga_o_0m
_cod_depositor_comments          'Adding full bibliography for 7133136.cif.'
_cod_database_code               7133136
_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:
 C002(H002), C00A(H00g), C00D(H00j)
2.b Secondary CH2 refined with riding coordinates:
 C005(H00a,H00b), C006(H00c,H00d), C009(H00e,H00f), C00C(H00h,H00i), C00E(H00k,
 H00l), C00G(H00p,H00q), C00H(H00r,H00s), C00I(H00t,H00u)
2.c Idealised Me refined as rotating group:
 C00F(H00m,H00n,H00o), C00K(H00x,H00y,H), C00L(H00z,Ha,Hb)
;
_olex2_submission_special_instructions 'No special instructions were received'