Total Synthesis of Ingenol
Andrew Nickel; Toru Maruyama; Haifeng Tang; Prescott D. Murphy; Blake Greene; Naeem Yusuff; John L. Wood; Journal of the American Chemical Society 126 (2004) 16300–16301; doi:10.1021/ja044123l

data_4113269
_publ_contact_author
;
     Prof. John L. Wood
     Department of Chemistry
     Yale University
     225 Prospect St
     PO Box 208107
     New Haven, CT 06520-8107
     USA
;
_publ_contact_author_email       john.wood@yale.edu
_publ_contact_author_fax         '+203 432 6144'
_publ_contact_author_phone       '+203 432 5991'
_publ_section_title
;
 Total Synthesis of Ingenol
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16300
_journal_page_last               16301
_journal_paper_doi               10.1021/ja044123l
_journal_volume                  126
_journal_year                    2004
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H36 O6 S'
_chemical_formula_weight         512.64
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.55(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.738(2)
_cell_length_b                   7.3775(15)
_cell_length_c                   15.207(3)
_cell_measurement_temperature    173(2)
_cell_volume                     1294.6(4)
_computing_cell_refinement       Denzo
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo
_computing_molecular_graphics    XP
_computing_publication_material  XCIF
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1390
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5866
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       needle
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5866
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1404
_refine_ls_R_factor_gt           0.0695
_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^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1535
_reflns_number_gt                3604
_reflns_number_total             5866
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja044123lsi20040927_034350.cif
_cod_data_source_block           an04
_cod_original_cell_volume        1294.7(4)
_cod_database_code               4113269