3-Hydr­oxy-3a,6,8c-trimethyl­perhydro­oxireno[2′,3′:7,8]naphtho[1,2-b]furan-7(2H)-one

Victor Kesternich; Paulina Cortés; Iván Brito; Alejandro Cárdenas; Matías López-Rodríguez

doi:10.1107/S1600536809025124

. 2009 Jul 4;65(Pt 8):o1777–o1778. doi: 10.1107/S1600536809025124

3-Hydroxy-3a,6,8c-trimethylperhydrooxireno[2′,3′:7,8]naphtho[1,2-b]furan-7(2H)-one

Victor Kesternich ^a, Paulina Cortés ^a, Iván Brito ^b,^*, Alejandro Cárdenas ^c, Matías López-Rodríguez ^d

PMCID: PMC2977239 PMID: 21583485

Abstract

The title compound, C₁₅H₂₂O₄, consists of two trans-fused six-membered rings and a trans-fused five-membered γ-lactone. The epoxy and hydroxyl groups are α-oriented. The cyclohexane rings adopt half-chair and chair conformations and the lactone ring is in an envelope conformation. The molecular structure is stabilized by one O—H⋯O and three C—H⋯O intramolecular hydrogen bonds.

Related literature

For background to sesquiterpene lactones, see: Fraga (2008 ▶). For their biological activity, see: Pillay et al. (2007 ▶); Ohno et al. (2005 ▶); Lindenmeyer et al. (2006 ▶). For synthetic details, see: Villar et al. (1983 ▶); González, et al. (1982 ▶). For a related structure, see: Rychlewska et al. (1982 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₁₅H₂₂O₄
M _r = 266.33
Monoclinic,
a = 8.251 (3) Å
b = 7.239 (2) Å
c = 11.434 (2) Å
β = 94.201 (5)°
V = 681.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 292 K
0.20 × 0.09 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: none
6696 measured reflections
1601 independent reflections
1495 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.108
S = 1.13
1601 reflections
179 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); 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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025124/pv2169sup1.cif

e-65-o1777-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025124/pv2169Isup2.hkl

e-65-o1777-Isup2.hkl^{(77.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.79 (4)	2.27 (4)	2.952 (3)	146 (5)
C9—H9A⋯O4	0.97	2.55	2.958 (3)	105
C5—H5⋯O4	0.98	2.57	2.925 (3)	101
C15—H15C⋯O2	0.96	2.53	2.913 (3)	104

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Acknowledgments

IB thanks the Spanish Research Council (CSIC) for providing a free-of-charge licence for the CSD system.

supplementary crystallographic information

Comment

Sesquiterpene lactones constitute a large group of natural products (Fraga, 2008). The eudesmanolides are natural products belong to the sesquiterpene lactones composed of fifteen carbon atoms. Many of these compounds, natural or synthetics, are of particular interest because of their biological activity (Pillay, et al., 2007; Ohno, et al., 2005; Lindenmeyer, et al., 2006). We report in this article the synthesis and crystal structure of a novel eudesmanolide, the title compound, (I).

The structure of the title compound (Fig. 1) is stabilized by one O—H···O and three C—H···O intramolecular hydrogen bonds (Table 1). The structure of (I) consists of two trans-fused [C(5)—C(10)] six-membered rings and a trans-fused [at C(6)—C(7)] five-membered γ-lactone. The epoxy and hidroxyl group are α -oriented. The cyclohexane rings adopt half-chair [C1/C2/C3/C4/C5/C10] and chair [C5/C6/C7/C8/C9/C10] and the lactone ring is in an envelope conformation respectively, as shown by the Cremer & Pople (1975) puckering parameters [Q_T=0.525 (2) Å, θ =46.9 (2)°, φ=321.1 (4)°; Q_T=0.616 (2) Å, θ =8.81 (2)°, φ=56.3 (1)°; q₂=0.382 (2) Å, φ₂=244.5 (3)°, respectively].

The crystal structure of the title compound is isomorphous with erivanin (Rychlewska et al., 1982).

Experimental

The title compound (I) was prepared by epoxidation of 1 with monoperoxyphthalic acid magnesium (MMPPA) at room temperature as shown in Fig. 2. In turn the product 1 was obtained by reduction of desoxyvulgarina(1-oxo-6β,7α,11β-H-eudesm-4-en-6,12-olide) (Villar et al., 1983), with sodium borohydride in ethanol (González, et al., 1982). Recrystallization from hexane/athyl acetate (3:1) at room temperature afforded colourless crystals suitable for X-ray diffraction analysis.