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_1515987
_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         'C40 H40 N2 O5 S2, C4 H8 O2'
_chemical_formula_sum            'C44 H49 N2 O7 S2'
_chemical_formula_weight         781.97
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-04-22
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_cell_angle_alpha                84.427(5)
_cell_angle_beta                 72.768(5)
_cell_angle_gamma                67.283(5)
_cell_formula_units_Z            2
_cell_length_a                   10.515(5)
_cell_length_b                   13.390(5)
_cell_length_c                   15.724(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1950.1(13)
_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      566(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10576
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.36
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.192
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             830
_refine_diff_density_max         0.637
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     512
_refine_ls_number_reflns         7096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0756
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1213P)^2^+3.2813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.2410
_reflns_number_gt                5087
_reflns_number_total             7096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501078d_si_005.cif
_cod_data_source_block           24maram
_cod_depositor_comments
'Adding full bibliography for 1515980--1515987.cif.'
_cod_database_code               1515987