Remarkable switch of regioselectivity in diels-alder reaction: divergent total synthesis of borreverine, caulindoles, and flinderoles.
Dethe, Dattatraya H.; Erande, Rohan D.; Dherange, Balu D.; Organic letters 16 (2014) 2764–2767; doi:10.1021/ol501078d

data_1515980
_publ_section_title
;
 Remarkable switch of regioselectivity in diels-alder reaction: divergent
 total synthesis of borreverine, caulindoles, and flinderoles.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2764
_journal_page_last               2767
_journal_paper_doi               10.1021/ol501078d
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C36 H44 N4 O4'
_chemical_formula_sum            'C36 H44 N4 O4'
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_symmetry_space_group_name_H-M   'P c a 21'
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.739(5)
_cell_length_b                   9.667(5)
_cell_length_c                   12.857(5)
_cell_measurement_reflns_used    4205
_cell_measurement_temperature    100(2)
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_cell_volume                     3199(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16615
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_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.994
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.078
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_refine_diff_density_max         0.279
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_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         5814
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_refine_ls_R_factor_all          0.0587
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_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0524P)^2^+0.5349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                5005
_reflns_number_total             5814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501078d_si_001.cif
_cod_data_source_block           12augb
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1515980--1515987.cif.
;
_cod_original_sg_symbol_Hall     'P 2c -2ac  '
_cod_original_sg_symbol_H-M      'Pca2(1) '
_cod_original_formula_sum        'C36 H44 N4 O4 '
_cod_database_code               1515980