Enantioselective Total Synthesis of Desbromoarborescidines A-C and the Formal Synthesis of (S)-Deplancheine
Pravat Mondal; Narshinha P. Argade; Journal of Organic Chemistry 78 (2013) 6802–6808; doi:10.1021/jo401079v

data_4028409
_publ_contact_author
;
Dr. N.P.Argade

Scientist
Organic Chemistry Division  
National Chemical Laboratory
Dr. Homi Bhaba Road
Pune 411008, India
;
_publ_section_title
;
 Enantioselective Total Synthesis of Desbromoarborescidines A-C and the
 Formal Synthesis of (S)-Deplancheine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6802
_journal_page_last               6808
_journal_paper_doi               10.1021/jo401079v
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H16 N2 O2'
_chemical_formula_sum            'C15 H16 N2 O2'
_chemical_formula_weight         256.30
_chemical_name_common            Compound-9
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-19
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.08.18 svn.r1932, GUI svn.r3819)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 100.383(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0484(2)
_cell_length_b                   12.2605(4)
_cell_length_c                   11.7640(3)
_cell_measurement_reflns_used    2719
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.0958
_cell_measurement_theta_min      3.0996
_cell_volume                     1283.70(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1640
_diffrn_measured_fraction_theta_full 0.9946
_diffrn_measured_fraction_theta_max 0.9673
_diffrn_measurement_details
;
  1 omega   47.00   95.00   1.0000   12.1800
omega____ theta____ kappa____ phi______ frames
    -       18.5831 -178.0000  -30.0000 48

  2 omega   49.00   84.00   1.0000   12.1800
omega____ theta____ kappa____ phi______ frames
    -       18.5831  178.0000   60.0000 35

  3 omega   37.00   87.00   1.0000   12.1800
omega____ theta____ kappa____ phi______ frames
    -       18.5831   57.0000  120.0000 50

  4 omega  -54.00   37.00   1.0000   12.1800
omega____ theta____ kappa____ phi______ frames
    -       18.5831  -37.0000    0.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0248793000
_diffrn_orient_matrix_UB_12      -0.0467821000
_diffrn_orient_matrix_UB_13      0.0265909000
_diffrn_orient_matrix_UB_21      0.0712711000
_diffrn_orient_matrix_UB_22      -0.0041665000
_diffrn_orient_matrix_UB_23      0.0365200000
_diffrn_orient_matrix_UB_31      -0.0255933000
_diffrn_orient_matrix_UB_32      0.0337713000
_diffrn_orient_matrix_UB_33      0.0414244000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5868
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.16
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'SuperNova (Mo) x-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description
;
;
_exptl_crystal_F_000             544.0
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(02)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.167
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.136
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1604
_refine_ls_wR_factor_ref         0.1717
_reflns_number_gt                3601
_reflns_number_total             3615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401079v_si_002.cif
_cod_data_source_block           Compound-9
_cod_database_code               4028409
_chemical_oxdiff_formula         'C8 N2 O2 H4'
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32