Meroterpenoid Synthesis via Sequential Polyketide Aromatization and Cationic Polyene Cyclization: Total Syntheses of (+)-Hongoquercin A and B and Related Meroterpenoids.
Ma, Tsz-Kan; Elliott, Daniel C.; Reid, Stephanie; White, Andrew J. P.; Parsons, Philip J.; Barrett, Anthony G. M.; The Journal of organic chemistry 83 (2018) 13276–13286; doi:10.1021/acs.joc.8b02095

data_4035745
_publ_section_title
;
 Meroterpenoid Synthesis via Sequential Polyketide Aromatization and
 Cationic Polyene Cyclization: Total Syntheses of (+)-Hongoquercin A and B
 and Related Meroterpenoids.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13276
_journal_page_last               13286
_journal_paper_doi               10.1021/acs.joc.8b02095
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H28 O5'
_chemical_formula_sum            'C21 H28 O5'
_chemical_formula_weight         360.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                94.713(4)
_cell_angle_beta                 102.968(4)
_cell_angle_gamma                114.675(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8319(4)
_cell_length_b                   10.1843(5)
_cell_length_c                   12.0790(6)
_cell_measurement_reflns_used    5580
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      73.7180
_cell_measurement_theta_min      3.8140
_cell_volume                     942.92(9)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.4115
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.980
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14928
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.859
_diffrn_reflns_theta_min         3.832
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
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    1.269
_exptl_crystal_description       'blocky needles'
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.2893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2964
_reflns_number_total             3734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02095_si_004.cif
_cod_data_source_block           41
_cod_original_cell_volume        942.91(9)
_cod_database_code               4035745
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              72405
_shelx_hkl_checksum              10664