Total synthesis of (+)- and (-)-sundiversifolide via intramolecular acylation and determination of the absolute configuration.
Ohtsuki, Keiko; Matsuo, Kazumasa; Yoshikawa, Takashi; Moriya, Chihiro; Tomita-Yokotani, Kaori; Shishido, Kozo; Shindo, Mitsuru; Organic letters 10 (2008) 1247–1250; doi:10.1021/ol8001333

data_1504584
_publ_section_title
;
 Total synthesis of (+)- and (-)-sundiversifolide via intramolecular
 acylation and determination of the absolute configuration.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1247
_journal_page_last               1250
_journal_paper_doi               10.1021/ol8001333
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C13 H18 O3 '
_chemical_formula_sum            'C13 H18 O3'
_chemical_formula_weight         222.28
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.0773(13)
_cell_length_b                   10.2119(14)
_cell_length_c                   12.5888(17)
_cell_measurement_reflns_used    15409
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      71.8
_cell_measurement_theta_min      3.5
_cell_volume                     1166.9(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  SHELXL
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16320
_diffrn_reflns_theta_full        71.78
_diffrn_reflns_theta_max         71.78
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.793
_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    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             480.00
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1322
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0771P)^2^+0.2932P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1447
_reflns_number_gt                1093
_reflns_number_total             1322
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol8001333-file003.cif
_cod_data_source_block           '_35g4169ar'
_cod_original_formula_sum        'C13 H18 O3 '
_cod_database_code               1504584