Total Synthesis of γ-Alkylidenebutenolides, Potent Melanogenesis Inhibitors from Thai Medicinal Plant Melodorum fruticosum.
Tanabe, Genzoh; Manse, Yoshiaki; Ogawa, Teppei; Sonoda, Naoki; Marumoto, Shinsuke; Ishikawa, Fumihiro; Ninomiya, Kiyofumi; Chaipech, Saowanee; Pongpiriyadacha, Yutana; Muraoka, Osamu; Morikawa, Toshio; The Journal of organic chemistry 83 (2018) 8250–8264; doi:10.1021/acs.joc.8b00986

data_4035559
_publ_section_title
;
 Total Synthesis of \g-Alkylidenebutenolides, Potent Melanogenesis
 Inhibitors from Thai Medicinal Plant Melodorum fruticosum.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8250
_journal_page_last               8264
_journal_paper_doi               10.1021/acs.joc.8b00986
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C30 H30 O5 Si '
_chemical_formula_sum            'C30 H30 O5 Si'
_chemical_formula_weight         498.65
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                   8.5428(4)
_cell_length_b                   17.2873(9)
_cell_length_c                   18.2419(8)
_cell_measurement_reflns_used    22124
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     2694.0(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25946
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.52
_refine_diff_density_min         -1.74
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  2690 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.763
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     356
_refine_ls_number_reflns         25946
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.0000
_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         0.0926
_reflns_number_gt                21762
_reflns_number_total             6165
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b00986_si_002.cif
_cod_data_source_block           '_TPPGT008b42-63a'
_cod_original_formula_sum        'C30 H30 O5 Si '
_cod_database_code               4035559