Enantioselective Synthesis of (-)-Terpestacin and (-)-Fusaproliferin: Clarification of Optical Rotational Measurements and Absolute Configurational Assignments Establishes a Homochiral Structural Series
Andrew G. Myers; Michael Siu; Feng Ren; Journal of the American Chemical Society 124 (2002) 4230–4232; doi:10.1021/ja020072l

data_4114751
_publ_section_title
;
 Enantioselective Synthesis of (-)-Terpestacin and (-)-Fusaproliferin:
 Clarification of Optical Rotational Measurements and Absolute
 Configurational Assignments Establishes a Homochiral Structural Series
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4230
_journal_page_last               4232
_journal_paper_doi               10.1021/ja020072l
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C25 H38 O4'
_chemical_formula_weight         402.55
_chemical_name_common            (-)-terpestacin
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 109.701(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.234(7)
_cell_length_b                   6.105(2)
_cell_length_c                   20.553(8)
_cell_measurement_temperature    213(2)
_cell_volume                     2390.3(15)
_computing_cell_refinement       'SMART (BRUKER, V5.054, 1998)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.01, 1999)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 1998, V5.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_method       '\w, 0.3 deg'
_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  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7942
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.6(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         5348
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1014P)^2^+0.0207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1611
_reflns_number_gt                4386
_reflns_number_total             5348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja020072l.cif
_cod_data_source_block           agm17t
_cod_original_cell_volume        2390.3(16)
_cod_database_code               4114751