Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by SmI2-Mediated Cyclization.
Fukaya, Keisuke; Tanaka, Yuta; Sato, Ayako C.; Kodama, Keisuke; Yamazaki, Hirohisa; Ishimoto, Takeru; Nozaki, Yasuyoshi; Iwaki, Yuki M.; Yuki, Yohei; Umei, Kentaro; Sugai, Tomoya; Yamaguchi, Yu; Watanabe, Ami; Oishi, Takeshi; Sato, Takaaki; Chida, Noritaka; Organic letters 17 (2015) 2570–2573; doi:10.1021/acs.orglett.5b01173

data_1520004
_publ_section_title
;
 Synthesis of Paclitaxel. 1. Synthesis of the ABC Ring of Paclitaxel by
 SmI2-Mediated Cyclization.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2570
_journal_page_last               2573
_journal_paper_doi               10.1021/acs.orglett.5b01173
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C29 H38 O8, 0.25(C5 H12)'
_chemical_formula_sum            'C30.25 H41 O8'
_chemical_formula_weight         532.64
_chemical_melting_point          509.2
_chemical_name_systematic
;(+-)-(1<i>SR</i>,5<i>SR</i>,6<i>SR</i>,7<i>SR</i>,10<i>SR</i>,11<i>SR</i>,13<i>RS</i>,14<i>SR</i>)-13-Hydroxy-7-methoxymethoxy-3-oxo-11,15,18,18-tetramethyl-2,4-dioxatetracyclo[12.3.1.0^1,5^.0^6,11^]octadec-15-en-10-yl 
benzoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                85.1124(14)
_cell_angle_beta                 78.3773(14)
_cell_angle_gamma                78.5231(15)
_cell_formula_units_Z            4
_cell_length_a                   11.3343(5)
_cell_length_b                   15.4666(7)
_cell_length_c                   16.4870(8)
_cell_measurement_reflns_used    9428
_cell_measurement_temperature    90.0
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.44
_cell_volume                     2771.3(2)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2014)'
_computing_data_collection       '<i>APEX2</i> (Bruker, 2014)'
_computing_data_reduction        '<i>SAINT</i> (Bruker, 2014)'
_computing_molecular_graphics    '<i>Mercury</i> (Macrae <i>et al.</i>, 2006)'
_computing_publication_material
'<i>publCif</i> (Westrip, 2010) and <i>PLATON</i> (Spek, 2009)'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXS2013</i> (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            50997
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '<i>SADABS</i> (Bruker, 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1146
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     726
_refine_ls_number_reflns         9735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+1.4256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                7339
_reflns_number_total             9735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01173_si_003.cif
_cod_data_source_block           A
_cod_depositor_comments
'Adding full bibliography for 1520002--1520004.cif.'
_cod_database_code               1520004