Facile entry to an efficient and practical enantioselective synthesis of a polycyclic cholesteryl ester transfer protein inhibitor.
Han, Zhengxu S.; Xu, Yibo; Fandrick, Daniel R.; Rodriguez, Sonia; Li, Zhibin; Qu, Bo; Gonnella, Nina C.; Sanyal, Sanjit; Reeves, Jonathan T.; Ma, Shengli; Grinberg, Nelu; Haddad, Nizar; Krishnamurthy, Dhileep; Song, Jinhua J.; Yee, Nathan K.; Pfrengle, Waldemar; Ostermeier, Markus; Schnaubelt, Jürgen; Leuter, Zeno; Steigmiller, Sonja; Däubler, Jürgen; Stehle, Emanuel; Neumann, Lukas; Trieselmann, Thomas; Tielmann, Patrick; Buba, Annette; Hamm, Rainer; Koch, Gunter; Renner, Svenja; Dehli, Juan R.; Schmelcher, Florian; Stange, Christian; Mack, Jürgen; Soyka, Rainer; Senanayake, Chris H.; Organic letters 16 (2014) 4142–4145; doi:10.1021/ol501833g

data_1517282
_publ_section_title
;
 Facile entry to an efficient and practical enantioselective synthesis of
 a polycyclic cholesteryl ester transfer protein inhibitor.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4142
_journal_page_last               4145
_journal_paper_doi               10.1021/ol501833g
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C27 H32 F3 N O3'
_chemical_formula_sum            'C27 H32 F3 N O3'
_chemical_formula_weight         475.56
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_date             2014-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.23 svn.r2946 for OlexSys, GUI svn.r4855)
;
_cell_angle_alpha                90
_cell_angle_beta                 127.987(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.7938(11)
_cell_length_b                   6.3604(3)
_cell_length_c                   18.1051(7)
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    100
_cell_measurement_theta_max      61.02
_cell_measurement_theta_min      3.10
_cell_volume                     2522.6(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9636
_diffrn_measured_fraction_theta_max 0.9636
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13430
_diffrn_reflns_theta_full        61.1394
_diffrn_reflns_theta_max         61.14
_diffrn_reflns_theta_min         4.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.7520
_exptl_absorpt_correction_T_min  0.6690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1477 before and 0.0317 after correction.
The Ratio of minimum to maximum transmission is 0.8896.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.2521
_exptl_crystal_F_000             1008.0
_refine_diff_density_max         1.1900
_refine_diff_density_min         -0.5508
_refine_diff_density_rms         0.0659
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_d_res_high            0.8802
_refine_ls_d_res_low             9.0432
_refine_ls_goodness_of_fit_ref   1.0566
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    49
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0566
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0903P)^2^+5.2134P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1478
_refine_special_details
;
associated with the CF3 group which has high thermal motion
data collection limited to 122 2theta due to instrument obstructions
;
_reflns_Friedel_coverage         0.950
_reflns_limit_h_max              31
_reflns_limit_h_min              -31
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                3704
_reflns_number_total             3734
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol501833g_si_002.cif
_cod_data_source_block           scan_01m_a
_cod_depositor_comments          'Adding full bibliography for 1517282.cif.'
_cod_database_code               1517282
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C16(H16), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C20(H20a,H20b), C22(H22a,H22b), C23(H23a,H23b), C24(H24a,H24b),
 C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'