Au-Catalyzed [2 + 3] Annulation of Enamides with Propargyl Esters: Total Synthesis of Cephalotaxine and Cephalezomine H.
Ma, Xiao-Yan; An, Xian-Tao; Zhao, Xian-He; Du, Ji-Yuan; Deng, Yu-Hua; Zhang, Xiang-Zhi; Fan, Chun-An; Organic letters 19 (2017) 2965–2968; doi:10.1021/acs.orglett.7b01202

data_1546074
_publ_section_title
;
 Au-Catalyzed [2 + 3] Annulation of Enamides with Propargyl Esters: Total
 Synthesis of Cephalotaxine and Cephalezomine H.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2965
_journal_page_last               2968
_journal_paper_doi               10.1021/acs.orglett.7b01202
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H25 N O4'
_chemical_formula_sum            'C24 H25 N O4'
_chemical_formula_weight         391.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 126.130(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.91(2)
_cell_length_b                   11.234(9)
_cell_length_c                   17.776(14)
_cell_measurement_reflns_used    2261
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.75
_cell_measurement_theta_min      2.81
_cell_volume                     4179(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10615
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.15
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0223(11)
_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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0587P)^2^+0.9004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                2197
_reflns_number_total             3868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b01202_si_002.cif
_cod_data_source_block           cis_3aa
_cod_depositor_comments
'Adding full bibliography for 1546073--1546077.cif.'
_cod_original_cell_volume        4178(6)
_cod_database_code               1546074
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1(0.088) H2(0.112) H3(0.123) H4(0.123) H5(0.099) H7A(0.074)
 H7B(0.074) H11A(0.08) H11B(0.08) H12(0.084) H14(0.061) H16(0.076) H17(0.1)
 H18(0.118) H19(0.11) H20(0.086) H21A(0.141) H21B(0.141) H21C(0.141)
 H22A(0.138) H22B(0.138) H22C(0.138) H24A(0.157) H24B(0.157) H24C(0.157)
 Fixed X: H1(0.1288) H2(0.0501) H3(-0.0418) H4(-0.058) H5(0.022) H7A(0.1634)
 H7B(0.1669) H11A(0.0499) H11B(0.0489) H12(0.1177) H14(0.1772) H16(0.2628)
 H17(0.347) H18(0.3758) H19(0.3207) H20(0.2358) H21A(0.0004) H21B(-0.0117)
 H21C(-0.0113) H22A(0.0661) H22B(0.0801) H22C(0.1358) H24A(0.3158) H24B(0.297)
 H24C(0.3447)
 Fixed Y: H1(0.2208) H2(0.0835) H3(0.0945) H4(0.2512) H5(0.3913) H7A(0.3754)
 H7B(0.3999) H11A(0.5035) H11B(0.6329) H12(0.4887) H14(0.7371) H16(0.4765)
 H17(0.4612) H18(0.6197) H19(0.7957) H20(0.8116) H21A(0.606) H21B(0.7061)
 H21C(0.7375) H22A(0.8911) H22B(0.8541) H22C(0.858) H24A(0.673) H24B(0.539)
 H24C(0.5994)
 Fixed Z: H1(0.1491) H2(0.0651) H3(0.0544) H4(0.1227) H5(0.2077) H7A(0.3126)
 H7B(0.2291) H11A(0.0733) H11B(0.038) H12(0.0199) H14(0.1856) H16(0.3011)
 H17(0.4557) H18(0.5537) H19(0.4964) H20(0.3418) H21A(0.1482) H21B(0.078)
 H21C(0.1643) H22A(0.2005) H22B(0.1291) H22C(0.2358) H24A(0.0777) H24B(0.072)
 H24C(0.1692)
;
_olex2_submission_special_instructions 'No special instructions were received'