Total Synthesis and Determination of the Absolute Configuration of 5,6-Dihydro-α-pyrone Natural Product Synargentolide B
Kavirayani R. Prasad; Phaneendra Gutala; Journal of Organic Chemistry 78 (2013) 3313–3322; doi:10.1021/jo400083v

data_4028096
_publ_contact_author_address
; 
 Department of Organic Chemistry
 Indian Institute of Science
 Bangalore, 560 012
 India
;
_publ_contact_author_email       prasad@orgchem.iisc.ernet.in
_publ_contact_author_fax         '(91) 80 2360 0529'
_publ_contact_author_name
; 
 'Prof. Kavirayani R. Prasad'
;
_publ_contact_author_phone       '(91) 80 2293 2524'
_publ_section_title
;
 Total Synthesis and Determination of the Absolute Configuration of
 5,6-Dihydro-\a-pyrone Natural Product Synargentolide B
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3313
_journal_page_last               3322
_journal_paper_doi               10.1021/jo400083v
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_compound_source        'see text'
_chemical_formula_moiety         'C20 H26 O10'
_chemical_formula_sum            'C20 H26 O10'
_chemical_formula_weight         426.41
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             'Jan 11 01:17:58 2013'
_audit_creation_method           'PLATON <TABLE ACC> option'
_cell_angle_alpha                90
_cell_angle_beta                 109.519(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2110(7)
_cell_length_b                   8.2737(3)
_cell_length_c                   19.509(1)
_cell_measurement_reflns_used    20663
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.7
_cell_volume                     2162.00(19)
_computing_cell_refinement       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) x-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_sigmaI/netI    0.0685
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20663
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         8405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0484P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                6759
_reflns_number_total             8405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400083v_si_001.cif
_cod_data_source_block           apf_120k
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4028096