Four nucleophilic additions to alkenynedioic acid derivatives in tandem; efficient one-pot synthesis of bicyclo[4.2.0]octenols.
Hata, Takeshi; Imade, Haduki; Urabe, Hirokazu; Organic letters 14 (2012) 2450–2453; doi:10.1021/ol300623j

data_1507668
_publ_section_title
;
 Four nucleophilic additions to alkenynedioic acid derivatives in tandem;
 efficient one-pot synthesis of bicyclo[4.2.0]octenols.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2450
_journal_page_last               2453
_journal_paper_doi               10.1021/ol300623j
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C37 H35 N O2'
_chemical_formula_sum            'C37 H35 N O2'
_chemical_formula_weight         525.69
_chemical_melting_point          191
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.521(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.4973(2)
_cell_length_b                   19.9091(7)
_cell_length_c                   21.8717(8)
_cell_measurement_reflns_used    6404
_cell_measurement_temperature    163.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     2828.23(17)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      163(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23163
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120.00
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     502
_refine_ls_number_reflns         6496
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1698
_reflns_number_gt                4507
_reflns_number_total             6496
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol300623j_si_002.cif
_cod_data_source_block           '__hata091105'
_cod_depositor_comments          'Adding full bibliography for 1507668.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507668