Total Syntheses of the Phytotoxic Lactones Herbarumin I and II and a Synthesis-Based Solution of the Pinolidoxin Puzzle
Alois Fürstner; Karin Radkowski; Conny Wirtz; Richard Goddard; Christian W. Lehmann; Richard Mynott; Journal of the American Chemical Society 124 (2002) 7061–7069; doi:10.1021/ja020238i

data_4114888
_publ_section_title
;
 Total Syntheses of the Phytotoxic Lactones Herbarumin I and II and a
 Synthesis-Based Solution of the Pinolidoxin Puzzle
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7061
_journal_page_last               7069
_journal_paper_doi               10.1021/ja020238i
_journal_volume                  124
_journal_year                    2002
_chemical_compound_source        'see paper'
_chemical_formula_sum            'C12.5 H20.5 Cl1.5 O5'
_chemical_formula_weight         303.96
_chemical_name_common            'Herbarumin II'
_chemical_name_systematic
; 
 2,7,8-trihydroxy-5-dodecen-9-olide
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_Int_Tables_number      92
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4709(6)
_cell_length_b                   9.4709(6)
_cell_length_c                   33.6977(16)
_cell_measurement_reflns_used    70211
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      1.00
_cell_volume                     3022.6(3)
_computing_cell_refinement       'Denzo / Scalepack (Otwinowski 1997)'
_computing_data_collection       'Collect software (Nonius, 1998)'
_computing_data_reduction        'Denzo / Scalepack (Otwinowski 1997)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD \w-scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.3 mm rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            6435
_diffrn_reflns_theta_full        23.24
_diffrn_reflns_theta_max         23.24
_diffrn_reflns_theta_min         4.22
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'XPREP, Siemens (1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0888
_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^)+(0.0753P)^2^+8.0084P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1996
_refine_ls_wR_factor_ref         0.2176
_reflns_number_gt                1578
_reflns_number_total             2099
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja020238i_2.cif
_cod_data_source_block           3880
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_formula_sum        'C12.50 H20.50 Cl1.50 O5'
_cod_database_code               4114888