Total Synthesis of the Potent cAMP Signaling Agonist (-)-Alotaketal A
Jinhua Huang; Jessica R. Yang; Jin Zhang; Jiong Yang; Journal of the American Chemical Society 134 (2012) 8806–8809; doi:10.1021/ja303529z

data_4117997
_publ_section_title
;
 Total Synthesis of the Potent cAMP Signaling Agonist (-)-Alotaketal A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8806
_journal_page_last               8809
_journal_paper_doi               10.1021/ja303529z
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration ab
_chemical_formula_sum            'C11 H15 Cl O3'
_chemical_formula_weight         230.68
_space_group_IT_number           80
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I 4bw'
_symmetry_space_group_name_H-M   'I 41'
_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                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.2294(4)
_cell_length_b                   18.2294(4)
_cell_length_c                   7.0465(3)
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      62.08
_cell_measurement_theta_min      4.85
_cell_volume                     2341.63(12)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            21338
_diffrn_reflns_theta_full        59.95
_diffrn_reflns_theta_max         59.95
_diffrn_reflns_theta_min         6.74
_exptl_absorpt_coefficient_mu    2.785
_exptl_absorpt_correction_T_max  0.9464
_exptl_absorpt_correction_T_min  0.7681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'colorless '
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       'plate     '
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1655
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+2.9662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                1559
_reflns_number_total             1655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja303529z_si_002.cif
_cod_data_source_block           jy
_cod_database_code               4117997