(1R,4R,5aS,7S,9aS)-7,9a-Dimethyl-6-methyl­ene-3-oxo-1,3,4,5,5a,6,7,8,9,9a-deca­hydro­naphtho­[1,2-c]furan-1,4-diyl diacetate

Mudyiwa, M.; Rajab, M.S.; Fronczek, F.R.; Watkins, S.F.

doi:10.1107/S1600536812033636

Volume 68
Part 9
Pages o2612-o2613
September 2012

Received 16 July 2012
Accepted 25 July 2012
Online 1 August 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R = 0.036
wR = 0.092
Data-to-parameter ratio = 28.2
Details

(1R,4R,5aS,7S,9aS)-7,9a-Dimethyl-6-methylene-3-oxo-1,3,4,5,5a,6,7,8,9,9a-decahydronaphtho[1,2-c]furan-1,4-diyl diacetate

Mercy Mudyiwa,^a Mohamed S. Rajab,^a Frank R. Fronczek ^a ^* and Steven F. Watkins ^a

^aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound, C₁₉H₂₄O₆, is a sesquiterpene lactone isolated from the Kenyan plant Warburgia ugandensis. Ring A adopts a chair conformation, ring B is in a C₂ twist conformation and the lactone ring is nearly planar with maximum deviation 0.007 (1) Å. The reported absolute configuration is based on that of the similar compound bromo-parasiticolide A and is supported by analysis of Bijvoet differences from light atoms in Mo K [alpha] radiation.

Related literature

For related structures, see: Fukuyama et al. (1975) (Bromo-parasiticolide A; PARASB); Ikhiri et al. (1995) (ZOXLIH); Aranda et al. (2001) (ABUKIR); King et al. (1973) (PRPRDE); Rossmann & Lipscomb (1958) (IRSBBZ); Rahbaek et al. (1997) (NEYKOR), Zhang et al. (2006) (UCOLAA, UCOKUT); Harinantenaina et al. (2007) (NIDJUG); McCorkindale et al. (1981) (PEBRLD); Hayashi et al. (2010) (VUTCIX). For the absolute configuration of sesquiterpene lactones, see: Fischer et al. (1979). For a description of the Cambridge Structural Database, see: Allen (2002). For the absolute configuration from Bijvoet pairs, see: Hooft et al. (2008). For compounds from Warburgia ugandensis, see: Wube et al. (2005) and for related compounds, see: Garland (1969); Kokwaro (1976).

Experimental

Crystal data

C₁₉H₂₄O₆
M_r = 348.38
Tetragonal, P 4₃ 2₁ 2
a = 13.014 (2) Å
c = 21.167 (3) Å
V = 3584.9 (9) Å³
Z = 8
Mo K radiation
= 0.10 mm^-1
T = 100 K
0.37 × 0.25 × 0.25 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) T_min = 0.966, T_max = 0.977
11378 measured reflections
6507 independent reflections
5934 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.092
S = 1.02
6507 reflections
231 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.21 e Å^-3
Absolute structure: Flack (1983). 2776 Bijvoet pairs
Flack parameter: 0.4 (6)

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5979 ).

Acknowledgements

Purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ESH-TR-13, administered by the Louisiana Board of Regents.

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Aranda, G., Moreno, L., Cortes, M., Prange, T., Maurs, M. & Azerad, R. (2001). Tetrahedron, 57, 6051-6056.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Fischer, N. H., Olivier, E. J. & Fischer, H. D. (1979). Progress in the Chemistry of Organic Natural Products, Vol. 38, edited by W. Hertz, H. Grisebach & G. W. Kirby. Vienna: Springer.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Fukuyama, K., Kawai, H., Tsukihara, T., Katsube, Y., Hamasaki, T., Hatsuda, Y. & Kuwano, H. (1975). Bull. Chem. Soc. Jpn, 48, 2949-2950.
Garland, M. T. (1969). An. Fac. Quim. Farm. U. Chile, 21, 108-110.
Harinantenaina, L., Asakawa, Y. & De Clercq, E. (2007). J. Nat. Prod. 70, 277-282.
Hayashi, N., Yamamoto, K., Minowa, N., Mitomi, M. & Nakada, M. (2010). Org. Biomol. Chem. 8, 1821-1825.
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.
Ikhiri, K., Mahaman, I., Ahond, A., Chiaroni, A., Poupat, C., Riche, C. & Potier, P. (1995). J. Nat. Prod. 58, 1136-1138.
King, T. J., Roberts, J. C. & Thompson, D. J. (1973). J. Chem. Soc. Perkin Trans. 1, pp. 78-80.
Kokwaro, J. O. (1976). Medicinal Plants of East Africa, p. 45. Nairobi: East African Lit. Bureau.
McCorkindale, N. J., Calzadilla, C. H., Hutchinson, S. A., Kitson, D. H., Ferguson, G. & Campbell, I. M. (1981). Tetrahedron, 37, 649-653.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Rahbaek, L., Christophersen, C., Frisvad, J., Bengaard, H. S., Larsen, S. & Rassing, B. R. (1997). J. Nat. Prod. 60, 811-813.
Rossmann, M. G. & Lipscomb, W. N. (1958). Tetrahedron, 4, 275-293.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wube, A. A., Bucar, F., Gibbons, S. & Asres, K. (2005). Phytochemistry, 66, 2309-2315.
Zhang, Y.-X., Jackson, S. H., Rajab, M. S., Fronczek, F. R. & Watkins, S. F. (2006). Acta Cryst. C62, o219-o221.