Synthesis, stereochemical analysis, and derivatization of myricanol provide new probes that promote autophagic tau clearance.
Martin, Mackenzie D.; Calcul, Laurent; Smith, Courtney; Jinwal, Umesh K.; Fontaine, Sarah N.; Darling, April; Seeley, Kent; Wojtas, Lukasz; Narayan, Malathi; Gestwicki, Jason E.; Smith, Garry R.; Reitz, Allen B.; Baker, Bill J.; Dickey, Chad A.; ACS chemical biology 10 (2015) 1099–1109; doi:10.1021/cb501013w

data_4512582
_publ_section_title
;
 Synthesis, stereochemical analysis, and derivatization of myricanol
 provide new probes that promote autophagic tau clearance.
;
_journal_issue                   4
_journal_name_full               'ACS chemical biology'
_journal_page_first              1099
_journal_page_last               1109
_journal_paper_doi               10.1021/cb501013w
_journal_volume                  10
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         '4(C21 H26 O5), 3.73(C4 H8 O), 0.37(O)'
_chemical_formula_sum            'C98.91 H133.82 O24.1'
_chemical_formula_weight         1708.39
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   49.7851(12)
_cell_length_b                   49.7851(12)
_cell_length_c                   6.7498(2)
_cell_measurement_temperature    100(2)
_cell_volume                     14488.4(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1407
_diffrn_reflns_av_sigmaI/netI    0.1116
_diffrn_reflns_limit_h_max       58
_diffrn_reflns_limit_h_min       -59
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            75183
_diffrn_reflns_theta_full        67.40
_diffrn_reflns_theta_max         67.42
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'INCOATEC Imus micro-focus source'
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.7289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             5520
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1242
_refine_ls_number_reflns         15952
_refine_ls_number_restraints     290
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0862
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1339P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2372
_reflns_number_gt                10771
_reflns_number_total             15952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cb501013w_si_005.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4512581--4512583.cif.'
_cod_original_formula_sum        'C98.91 H133.82 O24.10'
_cod_database_code               4512582