Highly Stereocontrolled Synthesis of Natural Barbacenic Acid, Novel Bisnorditerpene from Barbacenia flava
Amaury Patin; Alice Kanazawa; Christian Philouze; Andrew E. Greene; Estela Muri; Eliezer Barreiro; Paulo C. C. Costa; Journal of Organic Chemistry 68 (2003) 3831–3837; doi:10.1021/jo0340049

data_4022395
_publ_section_title
;
 Highly Stereocontrolled Synthesis of Natural Barbacenic Acid,
 Novel Bisnorditerpene from Barbacenia flava
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3831
_journal_page_last               3837
_journal_paper_doi               10.1021/jo0340049
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C19 H28 O4 '
_chemical_formula_sum            'C19 H28 O4'
_chemical_formula_weight         320.43
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2002-12-11
_audit_creation_method           'by teXsan v1.8'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.691(3)
_cell_length_b                   11.750(2)
_cell_length_c                   12.767(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      20.8
_cell_volume                     1753.8(6)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       \w
_diffrn_orient_matrix_UB_11      0.03003
_diffrn_orient_matrix_UB_12      -0.07783
_diffrn_orient_matrix_UB_13      0.01559
_diffrn_orient_matrix_UB_21      -0.03024
_diffrn_orient_matrix_UB_22      0.00572
_diffrn_orient_matrix_UB_23      0.07307
_diffrn_orient_matrix_UB_31      -0.07425
_diffrn_orient_matrix_UB_32      -0.03386
_diffrn_orient_matrix_UB_33      -0.02346
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.00
_diffrn_reflns_av_sigmaI/netI    0.020
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1810
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        74.90
_diffrn_reflns_theta_max         74.90
_diffrn_reflns_theta_min         3.46
_diffrn_standards_decay_%        -10.15
_diffrn_standards_interval_count 120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696.00
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.15
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.992
_refine_ls_goodness_of_fit_ref   1.992
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     208
_refine_ls_number_reflns         1527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0644
_refine_ls_shift/su_max          0.0036
_refine_ls_shift/su_mean         0.0007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00250|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.1023
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                1527
_reflns_number_total             1810
_reflns_threshold_expression     I>1.10\s(I)
_cod_data_source_file            jo0340049si20030213_095327_4.cif
_cod_data_source_block           C19O4H28
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C19 H28 O4 '
_cod_database_code               4022395