Efficient Asymmetric Synthesis ofabeo-Abietane-Type Diterpenoids by Using the Intramolecular Heck Reaction
Node, Manabu; Ozeki, Minoru; Planas, Loïc; Nakano, Masashi; Takita, Hirofumi; Mori, Daisuke; Tamatani, Shinji; Kajimoto, Tetsuya; Journal of Organic Chemistry 75 (2010) 190–196; doi:10.1021/jo901972b

data_4028964
_publ_section_title
;
 Efficient Asymmetric Synthesis ofabeo-Abietane-Type Diterpenoids by Using
 the Intramolecular Heck Reaction
;
_journal_coden_ASTM              JOCEAH
_journal_issue                   1
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              190
_journal_page_last               196
_journal_paper_doi               10.1021/jo901972b
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_sum            'C22 H29 Br O2'
_chemical_formula_weight         405.37
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_cell_angle_alpha                100.87(6)
_cell_angle_beta                 101.46(6)
_cell_angle_gamma                71.47(8)
_cell_formula_units_Z            2
_cell_length_a                   10.700(11)
_cell_length_b                   12.304(12)
_cell_length_c                   8.209(5)
_cell_measurement_reflns_used    17
_cell_measurement_temperature    133.1
_cell_measurement_theta_max      12.1
_cell_measurement_theta_min      11.1
_cell_volume                     995.1(16)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SHELXS97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.102
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9586
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.084
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.733
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             424.00
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         2.12
_refine_diff_density_min         -6.19
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  4578 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.708
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     516
_refine_ls_number_reflns         6257
_refine_ls_R_factor_gt           0.0952
_refine_ls_shift/su_max          1.4468
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0010Fo^2^ + 3.0000\s(Fo^2^) + 0.5000]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                6253
_reflns_number_total             9156
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_duplicate_entry             4025126
_cod_data_source_file            jo901972bsup1.cif
_cod_data_source_block           '_ST-357'
_cod_original_cell_volume        995.0(15)
_cod_original_formula_sum        'C44 H58 Br2 O4 '
_cod_database_code               4028964