Total Synthesis of (+)- seco-c Oleanane Via Stepwise. Controlled Radical Cascade Cyclization
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- Ὀφιοῦχος Παπαδάκης
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1 Supporting Information Total Synthesis of (+)- seco-c Oleanane Via Stepwise Controlled Radical Cascade Cyclization Victoriano Domingo, Jesús F. Arteaga, José Luis López Pérez, Rafael Pelaez, José F. Quílez del Moral,, * and Alejandro F. Barrero, * Department of Organic Chemistry, Institute of Biotechnology, Faculty of Sciences, University of Granada, Campus de Fuente Nueva, s/n,18071 Granada, Spain, Department of Chemistry Engineering, Physique Chemistry and Organic Chemistry, Faculty of Experimental Sciences, University of Huelva, Campus el Carmen, Huelva, Spain, Department of Pharmacy, University of Salamanca, Spain. afbarre@ugr.es, jfquilez@ugr.es S-1
2 TABLE OF CONTENTS General Experimental Section: S4 1 H and 13 C NMR Tables fonr natural and synthetic seco- C- oleanane (1) and C-ring seco-β amyrin (2): S5- S10 1 H and 13 C NMR spectra of 11: S11-S12 1 H and 13 C NMR spectra of 12: S13-S14 1 H and 13 C NMR spectra of 13: S15-S16 1 H and 13 C NMR spectra of 14: S17-S18 1 H and 13 C NMR spectra of 15: S19-S20 1 H and 13 C NMR spectra of 8: S21-S22 1 H and 13 C NMR spectra of 7: S23-S24 1 H and 13 C NMR spectra of 18: S25-S26 1 H and 13 C NMR spectra of 19: S27-S28 1 H and 13 C NMR spectra of 20: S29-S30 1 H and 13 C NMR spectra of 16: S31-S32 1 H NMR spectrum of synthetic 1: S33 1 H NMR spectrum of natural 1: S34 13 C NMR spectrum of synthetic 1: S35 13 C NMR spectrum of natural 1: S36 1 H and 13 C NMR spectra of synthetic 2: S37-S38 1 H and 13 C NMR spectra of synthetic 2: S39-S40 GC-MC of the mixture of 1, 3 and 4: S41- S42 1 H NMR spectrum of the mixture of 1, 3 and 4: S43 TOCSY experiments of the mixture of 1, 3 and 4: S44 S-2
3 Computational Methods: S45-S-67 S-3
4 General Details The solvents used were purified according to standard literature techniques and stored under Argon. THF and toluene were freshly distilled immediately prior to use from sodium/benzophenone and strictly deoxygenated for 30 min under Argon for each of the Cp 2 TiCl 2 /Mn or Zn reactions. Reagents were purchased at the higher commercial quality and used without further purification, unless otherwise stated. Reagents were purchased at the highest commercial quality and used without further purification, unless otherwise stated. Yields refer to chromatographically and spectroscopically ( 1 H NMR) homogeneous materials, unless otherwise stated.. Silica gel (35-70 µm) was used for flash column chromatography. Reactions were monitored by thin layer chromatography (TLC) using UV light as the visualizing agent and solutions of phosphomolybdic acid in ethanol or acidic mixture of anisaldehyde and heat as developing agents. HPLC with UV and RI detection was used. Semi-preparative HPLC separation were carried out on a column (5 µm Silica, 10 X 250 mm) at a flow rate of 2.0 ml/min. All air- and water-sensitive reactions were performed in flaks flame-dried under a positive flow of Argon and conducted under an Argon atmosphere. The following abbreviations were used to explain the multiplicities: s = singlet, d = doublet, t = triplet, q = quartet, quint = quintet, m = multiplet, pent = pentet, hex = hexet, br = broad. S-4
5 Table 1. 1 H NMR data comparison between synthetic seco- C- oleanane (1), and natural seco- C- oleanane (1) reported data 1. Synthetic seco- C- oleanane (1) 1 H NMR (CDCl 3, 500 MHz) (δ, multiplicity, coupling constant (Hz)) Natural seco- C- oleanane (1) 1 H NMR (CDCl 3, 300 MHz) (δ, multiplicity, coupling constant (Hz)) 4.86 (1H, d, J = 1.5 Hz, H-26) 4.87 (1H, d, J = 1.5 Hz, H-26) 4.63 (1Η, d, J = 1.0 Hz, H- 26 ) 4.62 (1Η, d, J = 1.0 Hz, H- 26 ) 3.25 (1H, dd, J = 11.8, 4.4 Hz, H-3) 3.24 (1H, dd, J = 11.7, 4.4 Hz, H-3) 2.41 (1H, ddd, J = 12.8, 4.2, 2.6 Hz, H-7) 2.39 (1H, dq, J = 12.7, 2.4 Hz, H-7) 1.99 (1H, m, H-7 ) 1.97 (1H, m, H-7 ) 2.32 and 1.47 (1H each, m, H-12, H-12 ) 2.32 and 1.47 (1H each, m, H-12, H-12 ) 1.99 and 1.88 (1H each, m, H-15, H-15 ) 1.97 and 1.87 (1H each, m, H-15, H-15 ) 1.89 and 0.81 (1H each, m, H-16, H-16 ) 1.89 and 0.80 (1H each, m, H-16, H-16 ) 1.79 (1H, t, J = 3.4 Hz) and 1.17 (1H, m), (H-1, H-1 ) 1.77 and 1.15 (1H each, m, H-1, H-1 ) 1.75 and 1.38 (1H each, m, H-6, H-6 ) 1.74 and 1.37 (1H each, m, H-6, H-6 ) 1.69 and 1.59 (1H each, m, H-2, H-2 ) 1.68 and 1.58 (1H each, m, H-2, H-2 ) 1.60 (1H, m, H-9) 1.59 (1H, m, H-9) 1.55 (1H, m, H-18) 1.55 (1H, m, H-18) 1.56 (3H, s, Me-27) 1.55 (3H, s, Me-27) 1.49 and 1.33 (1H each, m, H-11, H-11 ) 1.48 and 1.32 (1H each, m, H-11, H-11 ) 1 Roman, L. U.; Guerra-Ramirez, D.; Moran, G.; Martinez, I.; Hernandez, J. D.; Cerda-Garcia-Rojas, C. M.; Torres-Valencia, J. M.; Joseph-Nathan, P., Org. Lett., 2004, 6, S-5
6 1.48 and 1.21 (1H each, m, H-22, H-22 ) 1.47 and 1.21 (1H each, m, H-22, H-22 ) 1.34 and 0.93 (1H each, m, H-19, H-19 ) 1.33 and 0.92 (1H each, m, H-19, H-19 ) 1.33 and 1.12 (1H each, m, H-21, H-21 ) 1.32 and 1.10 (1H each, m, H-21, H-21 ) 1.10 (1H, dt, J = 12.8, 2.83Hz,, H-5) 1.06 (1H, m, H-5) 0.99 (3H, s, Me-23) 0.98 (3H, s, Me-23) 0.88 (3H, s, Me-30) 0.87 (3H, s, Me-30) 0.87 (3H, s, Me-29) 0.86 (3H, s, Me-29) 0.85 (3H, s, Me-28) 0.84 (3H, s, Me-28) 0.77 (3H, s, Me- 24) 0.76 (3H, s, Me- 24) 0.67 (3H, s, Me-25) 0.66 (3H, s, Me-25) Table C NMR data comparison between synthetic seco- C- oleanane (1), and natural seco- C- oleanane (1) reported data. Carbon no. Synthetic seco- C- oleanane (1) 13 C NMR (CDCl 3, 150 MHz) (δ) Natural seco- C- oleanane (1) 13 C NMR (CDCl 3, 75 MHz) (δ) S-6
7 S-7
8 Table 3. Comparison between 1 H NMR data of synthetic C- ring- seco- β- amyrin (2), and those of natural C- ring- seco- β- amyrin (2) reported data 2. Synthetic C- ring- seco- β- amyrin (2) 1 H NMR (CDCl 3, 500 MHz) (δ, multiplicity, coupling constant (Hz)) Natural C- ring- seco- β- amyrin (2) 1 H NMR (CDCl 3, 500 MHz) (δ, multiplicity, coupling constant (Hz)) 1.92, 1.19 (1H each, m, H-1, H-1 ) 1.92, 1.19 (1H each, m, H-1, H-1 ) (1H each, m, H-2, H-2 ) (1H each, m, H-2, H-2 ) 3.25 (1H, dd, J = 10.9, 4.9 Hz, H-3) 3.25 (1H, dd, J = 11.1, 4.8 Hz, H-3) 1.20 (1H, m, H-5) 1.20 (1H, m, H-5) 1.97 (1H each, m, H-6, H-6 ) 1.97 (1H each, m, H-6, H-6 ) 5.40 (1H, brs, H-7) 5.40 (1H, brs, H-7) 1.58 (1H, m, H-9) 1.58 (1H, m, H-9) 1.42, 1.14 (1H each, m, H-11, H-11 ) 1.42, 1.14 (1H each, m, H-11, H-11 ) 2.41 (1H, dt, J = 13.0, 5.8 Hz, H-12), 1.58 (1H, m, H-12 ) 2.41 (1H, dt, J = 12.8, 5.7 Hz, H-12), 1.58 (1H, m, H-12 ) 1.98, 1.87 (1H each, m, H-15, H-15 ) 1.98, 1.87 (1H each, m, H-15, H-15 ) 1.63 (1H, m, H-18) 1.63 (1H, m, H-18) 1.38, 0.98 (1H each, m, H-19, H-19 ) 1.38, 0.98 (1H each, m, H-19, H-19 ) 1.35, 1.13 (1H each, m, H-21, H-21 ) 1.35, 1.13 (1H each, m, H-21, H-21 ) 1.51, 1.23(1H each, m, H-22, H-22 ) 1.51, 1.23(1H each, m, H-22, H-22 ) 0.98 (3H, s, Me-23) 0.98 (3H, s, Me-23) 2 Shibuya M.; Xiang T.; Katsube Y.; Otsuka M.; Zhang H.; Ebizuka Y. J. Am. Chem. Soc., 2007, 129, S-8
9 0.86 (3H, s, Me-24) 0.86 (3H, s, Me-24) 0.76 (3H, s, Me-25) 0.76 (3H, s, Me-25) 1.75 (3H, brs, Me-26) 1.75 (3H, brs, Me-26) 1.57 (3H, s, Me-27) 1.57 (3H, s, Me-27) 0.84 (3H, s, Me-28) 0.84 (3H, s, Me-28) 0.88 (3H, s, Me-29) 0.88 (3H, s, Me-29) 0.88 (3H, s, Me-30) 0.88 (3H, s, Me-30) Table 4. Comparison between 13 C NMR data of synthetic synthetic C- ring- seco- β- amyrin (2), and those of natural C- ring- seco- β- amyrin (2) reported data. Carbon no. Synthetic C- ring- seco- β- amyrin (2) 13 C NMR (CDCl 3, 150 MHz) (δ) Natural C- ring- seco- β- amyrin (2) 13 C NMR (CDCl 3, 125 MHz) (δ) S-9
10 S-10
11 S f1 (ppm) TBSO SO 2 Ph 5 1 H-NMR 500 MHz CDCl3
12 f1 (ppm) 70 S TBSO 5 SO 2 Ph 13 C-NMR 125 MHz CDCl3
13 SO 2 Ph 1 H-NMR 500 MHz TBSO 12 CDCl 3 S-13
14 SO 2 Ph 13 C-NMR 125 MHz TBSO CDCl 3 12 S-14
15 SO 2 Ph TBSO 1 H-NMR 500 MHz 13 CDCl 3 S-15
16 SO 2 Ph TBSO C-NMR 125 MHz CDCl 3 S-16
17 SO 2 Ph TBSO 14 OH 1 H-NMR 500 MHz CDCl 3 S-17
18 SO 2 Ph OH 13 C-NMR 125 MHz TBSO CDCl 3 14 S-18
19 TBSO 15 OH OMEM 1 H-NMR 500 MHz CDCl 3 S-19
20 OH OMEM TBSO 13 C-NMR 125 MHz 15 CDCl 3 S-20
21 O OMEM 1 H-NMR 500 MHz TBSO 8 CDCl 3 S-21
22 O OMEM TBSO 8 13 C-NMR 125 MHz CDCl 3 S-22
23 MEMO TBSO 7 O 1 H-NMR 500 MHz CDCl 3 S-23
24 MEMO TBSO 7 O 13 C-NMR 125 MHz CDCl 3 S-24
25 S-25
26 S-26
27 S-27
28 S-28
29 S-29
30 S-30
31 S-31
32 S-32
33 S f1 (ppm)
34 Seco- C-oleanane (natural) S-34
35 S f1 (ppm) carbono STANDARD PROTON PARAMETERS
36 S-36
37 S f1 (ppm) 320_proton_500 P-695 RMN
38 S f1 (ppm) carbono STANDARD PROTON PARAMETERS
39 H HO 1 H-NMR 500 MHz CDCl 3 achilleol B (3) synthetic S-39
40 H HO 13 C-NMR 125 MHz CDCl 3 achilleol B (3) synthetic S-40
41 S-41
42 S-42
43 f1 (ppm) f1 (ppm) S-43
44 TOCSY correlation experiments H HO 1H-NMR 500 MHz CDCl3 3 seco-c- oleanane (1) H HO 2 achilleol B, 8,25 (3) H HO 1 camelliol A, 1,8 (4) f1 (ppm) S-44
45 Computational Details Conformational studies were performed for I to IV and IIIc to IVc with Spartan 08 3 previous to quantum mechanical optimization. The minimum energy conformations for I to IV depicted in Figure 1 are the ones closer to the transition state structures and were found to be the lowest energy conformations in THF. Geometry optimizations and energy calculations were performed with GAUSSIAN 09W 4 using DFT 5 method with ub3lyp/6-31+g(d) 6 basis set in vacuo. Transition state structures were optimized as saddle points at the same level b3lyp/6-31+g(d). A vibrational analysis was performed at the same level of theory in order to determine the zero-point vibrational energy and to characterize each stationary point as a minimum or transition state structure. Intrinsic reaction coordinate calculations 7 were also used to verify the identity of all transition-state structures. The reported energies are expressed en Hartrees (au). The same energies expressed in Kcal/mol as relative energies appear in Figure 1. 3 Shao, Y.; Molnar, L. F.; Jung, Y.; Kussmann, J.; Ochsenfeld, C.; Brown, S. T.; Gilbert, A. T. B.; Slipchenko, L. V.; Levchenko, S. V.; O'Neill, D. P.; DiStasio, R. A.; Lochan, R. C.; Wang, T.; Beran, G. J. O.; Besley, N. A.; Herbert, J. M.; Lin, C. Y.; Van Voorhis, T.; Chien, S. H.; Sodt, A.; Steele, R. P.; Rassolov, V. A.; Maslen, P. E.; Korambath, P. P.; Adamson, R. D.; Austin, B.; Baker, J.; Byrd, E. F. C.; Dachsel, H.; Doerksen, R. J.; Dreuw, A.; Dunietz, B. D.; Dutoi, A. D.; Furlani, T. R.; Gwaltney, S. R.; Heyden, A.; Hirata, S.; Hsu, C. P.; Kedziora, G.; Khalliulin, R. Z.; Klunzinger, P.; Lee, A. M.; Lee, M. S.; Liang, W.; Lotan, I.; Nair, N.; Peters, B.; Proynov, E. I.; Pieniazek, P. A.; Rhee, Y. M.; Ritchie, J.; Rosta, E.; Sherrill, C. D.; Simmonett, A. C.; Subotnik, J. E.; Woodcock, H. L.; Zhang, W.; Bell, A. T.; Chakraborty, A. K.; Chipman, D. M.; Keil, F. J.; Warshel, A.; Hehre, W. J.; Schaefer, H. F.; Kong, J.; Krylov, A. I.; Gill, P. M. W.; Head-Gordon, M., Phys. Chem. Chem. Phys. 2006, 8, Frisch, M. J. et al. Gaussian 09, revision A.02; Gaussian, Inc.; Wallingford, CT, (a) Lynch, B. J.; Zhao, Y.; Truhlar, D. G., J. Phys. Chem. A 2003, 107, (b) Koch, W.; Holthausen, M. C. A Chemist s Guide to Density Functional Theory,Wiley-VCH,Weinheim, Germany, 2 nd edn., 2000, pp (c) Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules, Clarendon Press, Oxford, UK, (a) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J., J. Phys. Chem. 1994, 98, (b) Kim, K., Jordan, K.D.; J. Phys. Chem 1994,.98, (c) Becke, A. D., J. Chem. Phys. 1993, 98, (d) Becke, A. D., J. Chem. Phys. 1993, 98, (f) Lee, C.; Yang, W.; Parr, R. G., Phys. Rev. B 1988, 37, (a) Gonzalez, C.; Schlegel, H. B. J. Phys. Chem. 1990, 94, (b) Fukui, K. Acc. Chem. Res. 1981, 14, S45
46 Cartesian Coordinates and Energies of I # opt freq ub3lyp/6-31+g(d) geom=connectivity Charge = -1 Multiplicity = C C C C C C C C C C C H H H H H H H H C H H C H H H H H C C H H H C C H H C C C H H C S46
47 H H H C H C H H H C H H H O H H C H H C C H H C H H H C H H H C H H H H H H SCF Done: E(UB3LYP) = A.U. after 3 cycles Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= S47
48 Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of TSI-->II # opt=(calcfc,ts) freq b3lyp/6-31+g(d) geom=connectivity Charge = -1 Multiplicity = C C C C C C C C C C C H H H H H H H H H H H C H H C H H H H H C H H H C C H H H S48
49 C C H H C C C H H C H H H C H C H H H C H H H O H H C H H C C H H C H H H C H H H SCF Done: E(UB3LYP) = Imag. Freq cm -1 A.U. after 29 cycles Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= S49
50 Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of II # opt freq ub3lyp/6-31+g(d) geom=connectivity Charge = -1 Multiplicity = C C C C C C C C C C C H H H H H H H H H H H C H H C H H H H H C H H H C S50
51 C H H H C C H H C C C H H C H H H C H C H H H C H H H O H H C H H C C H H C H H H C H H H SCF Done: E(UB3LYP) = A.U. after 3 cycles S51
52 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of TSII-->III # opt=(calcfc,ts) freq b3lyp/6-31+g(d) geom=connectivity Charge = -1 Multiplicity = C C C C C C C C C C C H H H H H H H H H H H C H H C H H H H H C S52
53 H H H C C H H H C C H H C C C H H C H H H C H C H H H C H H H O H H C H H C C H H C H H H C H H S53
54 H SCF Done: E(UB3LYP) = A.U. after 31 cycles Imag. Freq cm -1 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of III # opt freq ub3lyp/6-31+g(d) geom=connectivity Charge = -1 Multiplicity = C C C C C C C C C C C H H H H H H H H H H H C H H C H H S54
55 H H H C C H H H C C H H C C C H H C H H H C H C H H H C H H H O H H C H H C C H H C H H H C H H S55
56 H C H H H SCF Done: E(UB3LYP) = A.U. after 4 cycles Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of TSIII-->IV # opt=(calcfc,ts) freq b3lyp/6-31+g(d) geom=connectivity Charge = -1 Multiplicity = C C C C C C C C C C C H H H H H H H H H H H C H H S56
57 C H H H H H C H H H C C H H H C C H H C C C H H C H H H C H C H H H C H H H O H H C H H C C H H S57
58 C H H H C H H H SCF Done: E(UB3LYP) = A.U. after 4 cycles Imag. Freq cm -1 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of IV # opt freq ub3lyp/6-31+g(d) geom=connectivity Charge = -1 Multiplicity = C C C C C C C C C C C H H H H H H H H H H S58
59 H C H H C H H H H H C H H H C C H H H C C H H C C C H H C H H H C H C H H H C H H H O H H C H H S59
60 C C H H C H H H C H H H SCF Done: E(UB3LYP) = A.U. after 3 cycles Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= S60
61 Cartesian Coordinates and Energies of IIIc # opt freq ub3lyp/6-31+g(d) geom=connectivity Charge = +1 Multiplicity = C C C C C C C C C C C H H H H H H H H H H S61
62 H C H H C H H H H H C H H H C C H H H C C H H C C C H H C H H H C H C H H H C H H H O H H H C H S62
63 H C C H H C H H H C H H H SCF Done: E(UB3LYP) = A.U. after 3 cycles Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of TSIIIc-->IVc # opt=(calcall,tight,ts) freq b3lyp/6-31+g(d) geom=connectivity Charge = +1 Multiplicity = C C C C C C C C C C C H H H S63
64 H H H H H H H H C H H C H H H H H C H H H C C H H H C C H H C C C H H C H H H C H C H H H C H H S64
65 H O H H H C H H C C H H C H H H C H H H SCF Done: E(UB3LYP) = a.u. after 1 cycles Imag. Freq cm -1 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Cartesian Coordinates and Energies of IVc # opt freq ub3lyp/6-31+g(d) geom=connectivity Charge = +1 Multiplicity = C C C C C C C S65
66 C C C C H H H H H H H H H H H C H H C H H H H H C H H H C C H H H C C H H C C C H H C H H H C H S66
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