Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Radical Anion Cascade Triene Cyclization: Biomimetic Total Syntheses of Austalide Natural Products.
Ma, Tsz-Kan; Parsons, Philip J.; Barrett, Anthony G. M.; The Journal of organic chemistry 84 (2019) 4961–4970; doi:10.1021/acs.joc.9b00142

data_4034382
_publ_section_title
;
 Meroterpenoid Synthesis via Sequential Polyketide Aromatization and
 Radical Anion Cascade Triene Cyclization: Biomimetic Total Syntheses of
 Austalide Natural Products.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4961
_journal_page_last               4970
_journal_paper_doi               10.1021/acs.joc.9b00142
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C26 H34 O6'
_chemical_formula_sum            'C26 H34 O6'
_chemical_formula_weight         442.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 91.8761(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0357(2)
_cell_length_b                   18.1671(4)
_cell_length_c                   21.3736(4)
_cell_measurement_reflns_used    3190
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.0810
_cell_measurement_theta_min      4.1270
_cell_volume                     4670.91(16)
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15803
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.440
_diffrn_reflns_theta_min         4.139
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       plates
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         8939
_refine_ls_number_restraints     278
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+1.3153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5893
_reflns_number_total             8939
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00142_si_003.cif
_cod_data_source_block           15
_cod_original_cell_volume        4670.92(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4034382
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              18581
_shelx_hkl_checksum              23872