Toward a General Route to the Eunicellin Diterpenes: The Asymmetric Total Synthesis of Deacetoxyalcyonin Acetate
Gary A. Molander; David J. St. Jean; Julia Haas; Journal of the American Chemical Society 126 (2004) 1642–1643; doi:10.1021/ja0398464

data_4112235
_publ_section_title
;
 Toward a General Route to the Eunicellin Diterpenes: The Asymmetric Total
 Synthesis of Deacetoxyalcyonin Acetate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1642
_journal_page_last               1643
_journal_paper_doi               10.1021/ja0398464
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C20 H28 O6'
_chemical_formula_weight         364.42
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.22(3)
_cell_angle_beta                 104.700(19)
_cell_angle_gamma                90.45(3)
_cell_formula_units_Z            2
_cell_length_a                   13.906(9)
_cell_length_b                   5.635(3)
_cell_length_c                   14.432(9)
_cell_measurement_temperature    143(1)
_cell_volume                     1093.8(11)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0680
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4622
_diffrn_reflns_theta_full        22.46
_diffrn_reflns_theta_max         22.46
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.178
_refine_ls_extinction_coef       0.11(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.322
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.321
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.1252
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3121
_refine_ls_wR_factor_ref         0.3409
_reflns_number_gt                2746
_reflns_number_total             3796
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0398464si20031203_080212_2.cif
_cod_data_source_block           cmpd18
_cod_original_cell_volume        1093.8(12)
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               4112235