Total Synthesis of Manzamine A and Related Alkaloids
Pavol Jakubec; Alison Hawkins; Wolfgang Felzmann; Darren J. Dixon; Journal of the American Chemical Society 134 (2012) 17482–17485; doi:10.1021/ja308826x

data_4118828
_publ_contact_author             'Darren J Dixon'
_publ_contact_author_email       darren.dixon@chem.ox.ac.uk
_publ_section_title
;
 Total Synthesis of Manzamine A and Related Alkaloids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17482
_journal_page_last               17485
_journal_paper_doi               10.1021/ja308826x
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H26 N2 O7'
_chemical_formula_sum            'C19 H26 N2 O7'
_chemical_formula_weight         394.42
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_audit_creation_date             12-06-27
_audit_creation_method           CRYSTALS_ver_14.11
_cell_angle_alpha                90
_cell_angle_beta                 114.6519(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.3715(2)
_cell_length_b                   8.9189(2)
_cell_length_c                   11.0807(3)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     931.57(4)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.036
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8747
_diffrn_reflns_theta_full        26.374
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         5.102
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.9389
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.0002645
_refine_ls_shift/su_mean         0.0000235
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.31P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0881
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0881
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1752
_reflns_number_total             2253
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.18
_oxford_diffrn_Wilson_scale      4.23
_oxford_refine_ls_r_factor_ref   0.0610
_oxford_refine_ls_scale          0.4892(10)
_oxford_reflns_number_all        2253
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 002djd11
_cod_data_source_file            ja308826x_si_003.cif
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4118828
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  27,X'S) H   ( 272,X'S) H   ( 271,X'S) H   ( 273,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;