organic compounds
Methyl 2-(8a-hydroxy-4a-methyl-8-methylenedecahydronaphthalen-2-yl)acrylate
abLaboratoire de Chimie Biomoléculaire, Substances Naturelles et Réactivité, URAC 16, Faculté des Sciences Semlalia, BP 2390, Bd My Abdellah, 40000 Marrakech, Morocco, bUniversite Blaise Pascal, Laboratoire des Mate'riaux Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubie`re, France, and cLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia-Casablanca 20810 Mohammedia, Morocco
*Correspondence e-mail: mberraho@yahoo.fr
The title compound, C16H24O3, was synthesized from ilicic acid which was isolated from the aerial part of Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter]. The molecule contains two fused six-membered rings both in chair conformations. In the crystal, molecules are linked into chains running parallel to the a axis by O—H⋯O hydrogen bonds.
Related literature
For the synthesis, see: Barrero et al. (2009). For the medicinal and pharmacological properties of Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter], see: Shtacher & Kasshman (1970); Bohlmann et al. (1977); Chiappini et al. (1982); Azoulay et al. (1986); Bohlmann et al. (1977); Ceccherelli et al. (1988). For background to phytochemical studies of plants, see: Geissman & Toribio (1967). For see: Cremer & Pople (1975).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536811053712/bt5751sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811053712/bt5751Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811053712/bt5751Isup3.cml
To 1 g (4 mmol) of 2-(4a,8-Dimethyl-1,2,3,4,4a,5,6,7-octahydro- naphthalen-2-yl)- acrylic acid methyl ester dissolved in 40 ml of dichloromethane was added one equivalent of m-chloroperbenzoic acid at 70%. The reaction mixture was stirred at room temperature for 3 h, then treated three times with a solution of sodium bisulfite at 10%. The organic layer was then washed with distilled water three times until neutralization, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue obtained was chromatographed on silica gel eluting with hexane/ ethyl acetate (98/2) to give quantitatively the corresponding epoxide. 500 mg (1,89 mmol) of this epoxyde is dissolved with 5% of Para-toluene sulfonic acid (APTS) in 20 ml of dichloromethane. The reaction mixture was left stirring for a period of half an hour and then treated with 10 ml of a solution of sodium bicarbonate to 10%. The organic layer was dried filtered and concentrated under reduced pressure.
on silica gel, eluting with hexane/ethyl acetate (98/2) of the residue obtained, allowed us to obtain 250 mg (94.5 mmol) of the title compound which was recrystallized in dichloromethane.All H atoms were fixed geometrically and treated as riding with O—H = 0.82Å, C—H = 0.93 Å(aromatic), 0.96Å (methyl), 0.97 Å (methylene), 0.98Å (methine) with Uiso(H) = 1.2Ueq (Caromatic, Cmethylene, Cmethine) or Uiso(H) = 1.5Ueq (O, Cmethyl). In the absence of significant
the could not be determined and thus Friedel pairs were merged and any references to the were removed.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).C16H24O3 | F(000) = 576 |
Mr = 264.35 | Dx = 1.208 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 6881 reflections |
a = 6.0666 (5) Å | θ = 3.5–26.4° |
b = 10.0900 (9) Å | µ = 0.08 mm−1 |
c = 23.747 (2) Å | T = 296 K |
V = 1453.6 (2) Å3 | Prism, colourless |
Z = 4 | 0.65 × 0.45 × 0.26 mm |
Bruker APEXII CCD diffractometer | 1202 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.050 |
Graphite monochromator | θmax = 26.4°, θmin = 3.5° |
ϕ and ω scans | h = −7→7 |
6831 measured reflections | k = −11→12 |
1745 independent reflections | l = −29→29 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.0754P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
1745 reflections | Δρmax = 0.18 e Å−3 |
176 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (2) |
C16H24O3 | V = 1453.6 (2) Å3 |
Mr = 264.35 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.0666 (5) Å | µ = 0.08 mm−1 |
b = 10.0900 (9) Å | T = 296 K |
c = 23.747 (2) Å | 0.65 × 0.45 × 0.26 mm |
Bruker APEXII CCD diffractometer | 1202 reflections with I > 2σ(I) |
6831 measured reflections | Rint = 0.050 |
1745 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.18 e Å−3 |
1745 reflections | Δρmin = −0.19 e Å−3 |
176 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1942 (5) | 0.9387 (3) | 0.90963 (10) | 0.0356 (7) | |
H1A | 0.0601 | 0.9883 | 0.9026 | 0.043* | |
H1B | 0.1598 | 0.8451 | 0.9064 | 0.043* | |
C2 | 0.2754 (5) | 0.9680 (3) | 0.96934 (11) | 0.0383 (7) | |
H2 | 0.4089 | 0.9153 | 0.9756 | 0.046* | |
C3 | 0.3401 (6) | 1.1152 (3) | 0.97421 (12) | 0.0471 (8) | |
H3A | 0.2093 | 1.1697 | 0.9702 | 0.056* | |
H3B | 0.4019 | 1.1315 | 1.0112 | 0.056* | |
C4 | 0.5077 (5) | 1.1547 (3) | 0.92942 (12) | 0.0443 (8) | |
H4A | 0.6448 | 1.1082 | 0.9365 | 0.053* | |
H4B | 0.5369 | 1.2489 | 0.9326 | 0.053* | |
C4A | 0.4312 (5) | 1.1240 (3) | 0.86892 (11) | 0.0347 (7) | |
C5 | 0.6221 (5) | 1.1502 (3) | 0.82769 (12) | 0.0449 (8) | |
H5A | 0.6604 | 1.2435 | 0.8291 | 0.054* | |
H5B | 0.7500 | 1.1000 | 0.8397 | 0.054* | |
C6 | 0.5660 (6) | 1.1129 (4) | 0.76711 (13) | 0.0538 (9) | |
H6A | 0.6967 | 1.1222 | 0.7439 | 0.065* | |
H6B | 0.4549 | 1.1733 | 0.7528 | 0.065* | |
C7 | 0.4804 (5) | 0.9707 (3) | 0.76277 (12) | 0.0458 (8) | |
H7A | 0.4242 | 0.9554 | 0.7251 | 0.055* | |
H7B | 0.6012 | 0.9094 | 0.7691 | 0.055* | |
C8 | 0.3005 (5) | 0.9442 (3) | 0.80496 (11) | 0.0364 (7) | |
C8A | 0.3675 (4) | 0.9758 (3) | 0.86540 (11) | 0.0323 (7) | |
C9 | 0.1081 (5) | 0.9271 (3) | 1.01354 (12) | 0.0417 (8) | |
C10 | 0.1797 (6) | 0.9201 (3) | 1.07371 (12) | 0.0438 (8) | |
C11 | 0.4791 (6) | 0.9357 (4) | 1.13715 (12) | 0.0622 (10) | |
H11A | 0.4307 | 1.0140 | 1.1565 | 0.093* | |
H11B | 0.6373 | 0.9337 | 1.1364 | 0.093* | |
H11C | 0.4251 | 0.8586 | 1.1564 | 0.093* | |
C12 | 0.2369 (5) | 1.2136 (3) | 0.85384 (14) | 0.0507 (9) | |
H12A | 0.2844 | 1.3044 | 0.8537 | 0.076* | |
H12B | 0.1217 | 1.2024 | 0.8811 | 0.076* | |
H12C | 0.1824 | 1.1904 | 0.8172 | 0.076* | |
C13 | 0.1041 (5) | 0.8994 (3) | 0.79041 (12) | 0.0480 (8) | |
H13A | 0.0723 | 0.8829 | 0.7527 | 0.058* | |
H13B | −0.0025 | 0.8843 | 0.8178 | 0.058* | |
C15 | −0.0984 (6) | 0.8966 (4) | 1.00336 (14) | 0.0586 (10) | |
H15A | −0.1910 | 0.8724 | 1.0328 | 0.070* | |
H15B | −0.1520 | 0.8992 | 0.9667 | 0.070* | |
O1 | 0.5665 (3) | 0.9020 (2) | 0.87737 (8) | 0.0406 (5) | |
H1 | 0.5425 | 0.8225 | 0.8734 | 0.061* | |
O2 | 0.3955 (4) | 0.9371 (2) | 1.08027 (8) | 0.0514 (6) | |
O3 | 0.0589 (4) | 0.8972 (3) | 1.11270 (9) | 0.0684 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0353 (17) | 0.0361 (17) | 0.0354 (15) | −0.0003 (14) | 0.0008 (12) | 0.0014 (14) |
C2 | 0.0363 (17) | 0.0434 (19) | 0.0352 (15) | −0.0013 (15) | 0.0007 (12) | 0.0009 (14) |
C3 | 0.056 (2) | 0.047 (2) | 0.0380 (15) | −0.0083 (17) | 0.0031 (15) | −0.0083 (15) |
C4 | 0.049 (2) | 0.0409 (18) | 0.0430 (17) | −0.0123 (16) | −0.0021 (15) | −0.0041 (14) |
C4A | 0.0386 (17) | 0.0309 (16) | 0.0344 (13) | −0.0028 (13) | −0.0020 (13) | 0.0018 (12) |
C5 | 0.046 (2) | 0.0416 (19) | 0.0469 (17) | −0.0073 (16) | 0.0046 (15) | 0.0040 (15) |
C6 | 0.060 (2) | 0.057 (2) | 0.0444 (16) | −0.0056 (19) | 0.0084 (17) | 0.0056 (17) |
C7 | 0.055 (2) | 0.051 (2) | 0.0320 (14) | −0.0024 (17) | 0.0040 (14) | −0.0020 (15) |
C8 | 0.0417 (18) | 0.0327 (17) | 0.0348 (14) | 0.0041 (15) | −0.0043 (13) | −0.0010 (14) |
C8A | 0.0308 (17) | 0.0316 (16) | 0.0347 (14) | 0.0022 (12) | −0.0012 (12) | 0.0023 (13) |
C9 | 0.0396 (19) | 0.047 (2) | 0.0387 (14) | −0.0005 (16) | 0.0036 (13) | −0.0008 (15) |
C10 | 0.047 (2) | 0.046 (2) | 0.0386 (16) | −0.0012 (16) | 0.0038 (15) | 0.0002 (15) |
C11 | 0.062 (2) | 0.086 (3) | 0.0396 (16) | 0.001 (2) | −0.0049 (15) | −0.0004 (18) |
C12 | 0.055 (2) | 0.0378 (19) | 0.059 (2) | 0.0032 (16) | −0.0014 (16) | 0.0036 (17) |
C13 | 0.049 (2) | 0.056 (2) | 0.0389 (15) | −0.0014 (18) | −0.0085 (14) | −0.0026 (16) |
C15 | 0.044 (2) | 0.080 (3) | 0.0513 (19) | −0.008 (2) | 0.0048 (16) | 0.0058 (19) |
O1 | 0.0377 (12) | 0.0393 (12) | 0.0447 (11) | 0.0068 (10) | −0.0038 (9) | 0.0005 (11) |
O2 | 0.0436 (14) | 0.0750 (17) | 0.0354 (10) | −0.0031 (13) | 0.0001 (9) | 0.0007 (12) |
O3 | 0.0595 (16) | 0.103 (2) | 0.0431 (12) | −0.0137 (16) | 0.0125 (11) | 0.0082 (13) |
C1—C2 | 1.530 (4) | C7—C8 | 1.506 (4) |
C1—C8A | 1.533 (4) | C7—H7A | 0.9700 |
C1—H1A | 0.9700 | C7—H7B | 0.9700 |
C1—H1B | 0.9700 | C8—C13 | 1.320 (4) |
C2—C9 | 1.518 (4) | C8—C8A | 1.525 (4) |
C2—C3 | 1.541 (4) | C8A—O1 | 1.446 (3) |
C2—H2 | 0.9800 | C9—C15 | 1.312 (5) |
C3—C4 | 1.524 (4) | C9—C10 | 1.495 (4) |
C3—H3A | 0.9700 | C10—O3 | 1.203 (4) |
C3—H3B | 0.9700 | C10—O2 | 1.330 (4) |
C4—C4A | 1.541 (4) | C11—O2 | 1.443 (3) |
C4—H4A | 0.9700 | C11—H11A | 0.9600 |
C4—H4B | 0.9700 | C11—H11B | 0.9600 |
C4A—C12 | 1.528 (4) | C11—H11C | 0.9600 |
C4A—C5 | 1.539 (4) | C12—H12A | 0.9600 |
C4A—C8A | 1.547 (4) | C12—H12B | 0.9600 |
C5—C6 | 1.526 (4) | C12—H12C | 0.9600 |
C5—H5A | 0.9700 | C13—H13A | 0.9300 |
C5—H5B | 0.9700 | C13—H13B | 0.9300 |
C6—C7 | 1.530 (5) | C15—H15A | 0.9300 |
C6—H6A | 0.9700 | C15—H15B | 0.9300 |
C6—H6B | 0.9700 | O1—H1 | 0.8200 |
C2—C1—C8A | 111.5 (2) | C8—C7—C6 | 111.6 (3) |
C2—C1—H1A | 109.3 | C8—C7—H7A | 109.3 |
C8A—C1—H1A | 109.3 | C6—C7—H7A | 109.3 |
C2—C1—H1B | 109.3 | C8—C7—H7B | 109.3 |
C8A—C1—H1B | 109.3 | C6—C7—H7B | 109.3 |
H1A—C1—H1B | 108.0 | H7A—C7—H7B | 108.0 |
C9—C2—C1 | 111.9 (2) | C13—C8—C7 | 122.7 (3) |
C9—C2—C3 | 112.4 (2) | C13—C8—C8A | 124.0 (3) |
C1—C2—C3 | 109.8 (2) | C7—C8—C8A | 113.3 (2) |
C9—C2—H2 | 107.5 | O1—C8A—C8 | 107.5 (2) |
C1—C2—H2 | 107.5 | O1—C8A—C1 | 108.2 (2) |
C3—C2—H2 | 107.5 | C8—C8A—C1 | 114.2 (2) |
C4—C3—C2 | 111.7 (2) | O1—C8A—C4A | 106.2 (2) |
C4—C3—H3A | 109.3 | C8—C8A—C4A | 108.6 (2) |
C2—C3—H3A | 109.3 | C1—C8A—C4A | 111.7 (2) |
C4—C3—H3B | 109.3 | C15—C9—C10 | 116.3 (3) |
C2—C3—H3B | 109.3 | C15—C9—C2 | 125.1 (3) |
H3A—C3—H3B | 107.9 | C10—C9—C2 | 118.7 (3) |
C3—C4—C4A | 113.4 (3) | O3—C10—O2 | 122.3 (3) |
C3—C4—H4A | 108.9 | O3—C10—C9 | 124.6 (3) |
C4A—C4—H4A | 108.9 | O2—C10—C9 | 113.1 (3) |
C3—C4—H4B | 108.9 | O2—C11—H11A | 109.5 |
C4A—C4—H4B | 108.9 | O2—C11—H11B | 109.5 |
H4A—C4—H4B | 107.7 | H11A—C11—H11B | 109.5 |
C12—C4A—C5 | 109.2 (2) | O2—C11—H11C | 109.5 |
C12—C4A—C4 | 109.4 (2) | H11A—C11—H11C | 109.5 |
C5—C4A—C4 | 109.4 (2) | H11B—C11—H11C | 109.5 |
C12—C4A—C8A | 111.5 (2) | C4A—C12—H12A | 109.5 |
C5—C4A—C8A | 108.6 (2) | C4A—C12—H12B | 109.5 |
C4—C4A—C8A | 108.6 (2) | H12A—C12—H12B | 109.5 |
C6—C5—C4A | 112.9 (3) | C4A—C12—H12C | 109.5 |
C6—C5—H5A | 109.0 | H12A—C12—H12C | 109.5 |
C4A—C5—H5A | 109.0 | H12B—C12—H12C | 109.5 |
C6—C5—H5B | 109.0 | C8—C13—H13A | 120.0 |
C4A—C5—H5B | 109.0 | C8—C13—H13B | 120.0 |
H5A—C5—H5B | 107.8 | H13A—C13—H13B | 120.0 |
C5—C6—C7 | 111.8 (3) | C9—C15—H15A | 120.0 |
C5—C6—H6A | 109.3 | C9—C15—H15B | 120.0 |
C7—C6—H6A | 109.3 | H15A—C15—H15B | 120.0 |
C5—C6—H6B | 109.3 | C8A—O1—H1 | 109.5 |
C7—C6—H6B | 109.3 | C10—O2—C11 | 117.1 (2) |
H6A—C6—H6B | 107.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 2.24 | 3.033 (4) | 161 |
Symmetry code: (i) x+1/2, −y+3/2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C16H24O3 |
Mr | 264.35 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 6.0666 (5), 10.0900 (9), 23.747 (2) |
V (Å3) | 1453.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.65 × 0.45 × 0.26 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6831, 1745, 1202 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.114, 1.04 |
No. of reflections | 1745 |
No. of parameters | 176 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.19 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3i | 0.82 | 2.24 | 3.033 (4) | 161 |
Symmetry code: (i) x+1/2, −y+3/2, −z+2. |
Acknowledgements
We thank Professor Daniel Avignant for the data collection.
References
Azoulay, P., Reynier, J. P., Balansard, G., Gasquet, M. & Timon-David, P. (1986). Pharm. Acta Helv. 61, 345–352. CAS PubMed Web of Science Google Scholar
Barrero, A. F., Herrador, M. M., Arteaga, J. & Catalań, V. (2009). Eur. J. Org. Chem. pp. 3589–3594. Web of Science CrossRef Google Scholar
Bohlmann, F., Czerson, H. & Schoneweib, S. (1977). Chem. Ber. 110, 1330–1334. CrossRef CAS Web of Science Google Scholar
Bruker, (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ceccherelli, P., Curini, M. & Marcotullio, M. C. (1988). J. Nat. Prod. 51, 1006–1009. CrossRef CAS PubMed Web of Science Google Scholar
Chiappini, I., Fardella, G., Menghini, A. & Rossi, C. (1982). Planta Med. 44, 159–161. CrossRef PubMed CAS Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Geissman, T. A. & Toribio, F. P. (1967). Phytochemistry, 6, 1563–1567. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shtacher, G. & Kasshman, Y. (1970). J. Med. Chem. 13, 1221–1223. CrossRef CAS PubMed Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The Inula Viscosa (L) is widespread in Mediterranean area and extends to the Atlantic cost of Morocco. It is a well known medicinal plant (Shtacher & Kasshman, 1970; Chiappini et al., 1982) and has some pharmacological activities (Azoulay et al., 1986). This plant has been the subject of chemical investigation in terms of isolating sesquiterpene lactones (Bohlmann et al., 1977), sesquiterpene acids (Ceccherelli et al., 1988; Geissman & Toribio, 1967). The ilicic acid is one of the main components of the dichloromethane extract of the Inula Viscosa (L) Aiton or Dittrichia Viscosa (L) Greuter]. The literature report one article on the transformation of the ilicic acid (Barrero et al., 2009). In order to prepare products with high added value, that can be used in the pharmacologycal industry, we have studied the reactivity of this sesquiterpene acid. Thus, from this acid, we have prepared by the method of Barrero et al. (2009), 2-(4a,8-Dimethyl-1, 2,3,4,4 a,5,6,7- octahydro naphthalen-2-yl)-acrylic acid methyl ester. The epoxidation of the latter compound by metachloroperbenzoic acid (mCPBA), followed by the opening of the epoxide obtained by Bi(OTf)3 leads to the title compound (I) with a yield of 50%.
The molecule is built up from two fused six-membered rings. The molecular structure of (Fig. 1) shows the two rings to adopt a perfect chair conformation as indicated by Cremer & Pople (1975) puckering parameters Q(T)= 0.573 (3)Å and spherical polar angle θ = 176.9 (3)° with ϕ = 281 (8)° for the first ring (C1,C6··· C10) and Q(T)= 0.571 (3)Å with a spherical polar angle θ = 173.0 (3)° and ϕ = 144 (3)° for the second ring (C1, C6···C10) (Cremer and Pople,1975). Molecules are linked by intermolecular O—H···O hydrogen bonds (Table 1, Figure 2) to chains running parallel to the a axis.