An Expedient Route to Montanine-Type Amaryllidaceae Alkaloids: Total Syntheses of (-)-Brunsvigine and (-)-Manthine
An-Wei Hong; Tsung-Hui Cheng; Vellingiri Raghukumar; Chin-Kang Sha; Journal of Organic Chemistry 73 (2008) 7580–7585; doi:10.1021/jo801089y

data_4023706
_publ_contact_author_address
;
Department of Chemistry, 
National Tsing Hua University,
Hsinchu 300, Taiwan, ROC
;
_publ_contact_author_email       cksha@mx.nthu.edu.tw
_publ_contact_author_fax         '+886 3 5725870'
_publ_contact_author_name        'Dr. Chin-Kang Sha'
_publ_contact_author_phone       '+886 3 5722427'
_publ_section_title
;
 An Expedient Route to Montanine-Type Amaryllidaceae Alkaloids:
 Total Syntheses of (-)-Brunsvigine and (-)-Manthine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7580
_journal_page_last               7585
_journal_paper_doi               10.1021/jo801089y
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C23 H31 N O6 S'
_chemical_formula_weight         449.55
_chemical_name_common            'Pivaloate ester'
_chemical_name_systematic
; 
 (3aR,4aS,7R,8aS)-2,2-Dimethyl-5-[(4-methylphenyl)
sulfonyl]-4,4a,5,6,7,8a-hexahydro-3aH-[1,3]dioxolo
-[4,5-f]indol-7-yl pivalate.
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0221(2)
_cell_length_b                   11.0913(4)
_cell_length_c                   35.6702(7)
_cell_measurement_reflns_used    2721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     2382.52(13)
_computing_cell_refinement       'Siemens Smart'
_computing_data_collection       'Siemens Smart CCD'
_computing_data_reduction        'Siemens Saint'
_computing_molecular_graphics    'Siemens Shelxtl'
_computing_publication_material  'Siemens Shelxtl'
_computing_structure_refinement  'Siemens SHELXTL PLUS (VNS)'
_computing_structure_solution    'Siemens SHELXTL PLUS (VNS)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_av_sigmaI/netI    0.1740
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            13883
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.92345
_exptl_absorpt_correction_T_min  0.80480
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Columnar
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.30(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         5184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.1935
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0690P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1788
_reflns_number_gt                2201
_reflns_number_total             5184
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo801089y_si_002.cif
_cod_data_source_block           mr11nsad
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023706