Synthesis of the norjatrophane diterpene (-)-15-acetyl-3-propionyl- 17-norcharaciol.
Helmboldt, Hannes; Köhler, Daniel; Hiersemann, Martin; Organic letters 8 (2006) 1573–1576; doi:10.1021/ol060115t

data_1505894
_publ_section_title
;
 Synthesis of the norjatrophane diterpene (-)-15-acetyl-3-propionyl-
 17-norcharaciol.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1573
_journal_page_last               1576
_journal_paper_doi               10.1021/ol060115t
_journal_volume                  8
_journal_year                    2006
_chemical_absolute_configuration rm
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C15 H30 O3 Si'
_chemical_formula_sum            'C15 H30 O3 Si'
_chemical_formula_weight         286.48
_chemical_melting_point          388.65
_chemical_name_systematic        vinylcyclopentan
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2150(10)
_cell_length_b                   7.5240(10)
_cell_length_c                   16.782(3)
_cell_measurement_temperature    198(2)
_cell_volume                     910.3(2)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Schakal-99 (E.Keller 1999)'
_computing_publication_material  'XCIF 6.12 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_pressure         0.0
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22276
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         4.86
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS 2.03.(Sheldrick,Bruker AXS Inc.,2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.045
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_recrystallization_method
'from hexane/ethyl acetate; room temperature'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         3291
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0562P)^2^+0.1230P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                2822
_reflns_number_total             3291
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060115tsi20060115_080242.cif
_cod_data_source_block           hir-157
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1505894