Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of ( )-9a-epi-Hippocasine
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1 Supporting Information for: Iterative Synthetic Strategy for Azaphenalene Alkaloids. Total Synthesis of ( )-9a-epi-Hippocasine Sílvia Alujas-Burgos, Cristina Oliveras-González, Ángel Álvarez-Larena, Pau Bayón, * and Marta Figueredo, * Departament de Química, Universitat Autònoma de Barcelona, Bellaterra, Spain Servei de Difracció de Raigs X, Universitat Autònoma de Barcelona, Bellaterra, Spain INDEX 1 H- and 13 C-NMR spectra of compound 11 (two diastereomers) S-2 1 H- and 13 C-NMR spectra of compound 12 S-3 1 H- and 13 C-NMR spectra of compound 13 S-4 1 H-NMR spectrum of the aldehyde precursor of 14 S-5 1 H- and 13 C-NMR spectra of compound 14 (two diastereomers) S-6 1 H- and 13 C-NMR spectra of compound 15 (two diastereomers) S-7 Selective noe spectrum of compound 15 S-8 1 H-NMR study of the reduction of 14 S-9 1 H-NMR spectra of compounds 16 and 17 S-10 1 H- and 13 C-NMR spectra of compound 18 S-11 1 H- and 13 C-NMR spectra of compound 19 S-12 Selective noe Spectra of compound 19 S-13 1 H- and 13 C-NMR spectra of ( )-9a-epi-hippocasine TFA S-14 X-Ray analysis of compound 13 S-15 S-1
2 Compound 11 (two diastereomers) Figure S1. 1 H-NMR (250 MHz, CDCl 3 ) Figure S2. 13 C NMR (101 MHz, CDCl 3 ) S-2
3 Compound 12 Figure S3. 1 H-NMR (360 MHz, CDCl 3 ) Figure S4. 13 C-NMR (91 MHz, CDCl 3 ) S-3
4 Compound 13 Figure S5. 1 H-NMR (250 MHz, CDCl 3 ) Figure S6. 13 C-NMR (101 MHz, CDCl 3 ) S-4
5 Aldehyde precursor of 14 Figure S7. 1 H-NMR (250 MHz, CDCl 3 ) S-5
6 Compound 14 (two diastereomers) Figure S8. 1 H-NMR (400 MHz, CDCl 3 ) Figure S9. 13 C-NMR (101 MHz, CDCl 3 ) S-6
7 Compound 15 (two diastereomers) Figure S10. 1 H-NMR (400 MHz, CDCl 3 ) Figure S C-NMR (101 MHz, CDCl 3 ) S-7
8 Figure S12. Selective noe spectrum (360 MHz, CDCl 3 ) of triene 15 at 4.12 ppm. noe (400 MHz, CDCl 3 ) H-7 + H-3 H-2 H-2 H-1 H-6 H- H-9a 2H-1 H-7 H-1 H-6 H-4 H-9a H-1 S-8
9 Figure S13. 1 H-NMR (250 MHz, CDCl 3 ) study of the reduction of 14 over 4 h a) before addition of Red-Al (14) b) t=1 h c) t=2 h d) t=3 h e) t=4 h S-9
10 Compound 16 Figure S14. 1 H-NMR (250 MHz, CDCl 3 ) Compound 17 Figure S15. 1 H-NMR (250 MHz, CDCl 3 ) S-10
11 Compound 18 Figure S16. 1 H-NMR (400 MHz, CDCl 3 ) Figure S C-NMR (101 MHz, CDCl 3 ) S-11
12 Compound 19 Figure S18. 1 H-NMR (250 MHz, CDCl 3 ) Figure S C-NMR (63 MHz, CDCl 3 ) S-12
13 Figure S20. Selective noe spectra (400 MHz, CDCl 3 ) of tricycle 19 at 4.01, 3.29 and 2.67 ppm. H-7 + H- H-6 H-6a H-3a H-9a H-7 H-6 H-6a H-3a H-6a H-3a H-9a S-13
14 ( )-9a-epi-hippocasine TFA Figure S21. 1 H-NMR (400 MHz, CDCl 3 ) Figure S C-NMR (101 MHz, CDCl 3 ) S-14
15 X-Ray analysis of compound 13 Adequate crystals were obtained by crystallization from AcOEt/hexane. Data were collected using Mo Ka radiation in a SMART-APEX diffractometer. An empirical absorption correction was applied (SADABS). The structure was solved by direct methods (SHELXS-86) and refined by full-matrix least-squares methods on F 2 for all reflections (SHELXL-2016). Non-hydrogen atoms were refined anisotropically. Hydrogen atoms bonded to carbon atoms were placed in calculated positions with isotropic displacement parameters fixed at 1.5 (methyl hydrogen atoms) or 1.2 (the rest) times the U eq of the corresponding carbon atoms. For the methyl group, a rotating group refinement was applied. The hydroxylic hydrogen atom was located in a difference Fourier map and a rotating group refinement was applied using an isotropic displacement parameter fixed at 1.5 times the U eq of the corresponding oxygen atom. Crystal data and further refinement details are presented in Table 1. The crystal structure has been deposited at the CCDC and allocated the deposition number CCDC Table S1. Crystal data and structure refinement for compound 13. Empirical formula C 11 H 17 N O 2 Formula weight Temperature 296(2) K Wavelength Å Crystal system Orthorhombic Space group P Unit cell dimensions a = (4) Å α= 90. b = (5) Å β= 90. c = (5) Å γ = 90. Volume (8) Å 3 Z 4 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 424 Crystal size 0.50 x 0.49 x 0.42 mm 3 Theta range for data collection to Index ranges -10<=h<=10, -14<=k<=14, -15<=l<=16 Reflections collected 8405 Independent reflections 2558 [R(int) = ] Completeness to theta = % Absorption correction Semi-empirical from equivalents Max. and min. transmission 1 and S-15
16 Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 2558 / 0 / 129 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Absolute structure parameter 0.0(2) Largest diff. peak and hole and e.å -3 Figure S23. Thermal ellipsoid plot. The ellipsoid contour probability level is 50% S-16
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