Total synthesis and structural confirmation of ent-galbanic acid and marneral.
Corbu, Andrei; Perez, Manuel; Aquino, Maurizio; Retailleau, Pascal; Arseniyadis, Simeon; Organic letters 10 (2008) 2853–2856; doi:10.1021/ol8010216

data_1504753
_publ_section_title
;
 Total synthesis and structural confirmation of ent-galbanic acid and
 marneral.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2853
_journal_page_last               2856
_journal_paper_doi               10.1021/ol8010216
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C20 H40 O2 Si'
_chemical_formula_sum            'C20 H40 O2 Si'
_chemical_formula_weight         340.61
_chemical_name_systematic
; 
 2-((1R,2R,3R)-2-((tert-butyldimethylsilyloxy)methyl)
-2,3-dimethyl-6-(propan-2-ylidene)cyclohexyl)ethanol 
;
_space_group_IT_number           80
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'I 4bw'
_symmetry_space_group_name_H-M   'I 41'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.631(7)
_cell_length_b                   24.631(7)
_cell_length_c                   7.397(3)
_cell_measurement_reflns_used    1985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.028
_cell_measurement_theta_min      0.407
_cell_volume                     4488(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_sigmaI/netI    0.0592
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            7250
_diffrn_reflns_theta_full        19.13
_diffrn_reflns_theta_max         19.13
_diffrn_reflns_theta_min         2.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.008
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       hair
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1022
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0516P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0982
_reflns_number_gt                799
_reflns_number_total             1024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol8010216-file002.cif
_cod_data_source_block           mape348c
_cod_original_sg_symbol_H-M      I41
_cod_database_code               1504753