Total Synthesis of (-)-Martinellic Acid via Radical Addition-Cyclization-Elimination Reaction
Atsushi Shirai; Okiko Miyata; Norimitsu Tohnai; Mikiji Miyata; David J. Procter; David Sucunza; Takeaki Naito; Journal of Organic Chemistry 73 (2008) 4464–4475; doi:10.1021/jo800560p

data_4023482
_publ_section_title
;
 Total Synthesis of (-)-Martinellic Acid via Radical
 Addition-Cyclization-Elimination Reaction
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4464
_journal_page_last               4475
_journal_paper_doi               10.1021/jo800560p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C16 H16 N2 O4 '
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_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             2008-01-24
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   6.5797(3)
_cell_length_b                   13.1538(6)
_cell_length_c                   16.1049(6)
_cell_measurement_reflns_used    4521
_cell_measurement_temperature    213.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.4
_cell_volume                     1393.85(10)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR2004
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.094
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14428
_diffrn_reflns_theta_full        68.17
_diffrn_reflns_theta_max         68.17
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  0.771
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  1021 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2494
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0691P)^2^+0.2070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1532
_reflns_number_gt                2070
_reflns_number_total             2494
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo800560p-File003.cif
_cod_data_source_block           '_080123'
_cod_original_formula_sum        'C16 H16 N2 O4 '
_cod_database_code               4023482