(3R,4R,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one

Gille, A.; Schürmann, M.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536809050399

organic compounds

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Volume 65| Part 12| December 2009| Page o3274

doi:10.1107/S1600536809050399

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(3R,4R,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one

Annika Gille,^a Markus Schürmann,^a Hans Preut ^a ^* and Martin Hiersemann ^a

^aFakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
^*Correspondence e-mail: hans.preut@udo.edu

(Received 18 November 2009; accepted 23 November 2009; online 28 November 2009)

The relative configuration of the title compound, C₁₁H₁₈O₃, which was synthesized using a catalytic asymmetric Gosteli–Claisen rearrangement, a diastereoselective reduction with K-Selectride and an Evans aldol addition, was corroborated by single-crystal X-ray diffraction analysis. The five-membered ring has an envelope conformation with a dihedral angle of 29.46 (16)° between the coplanar part and the flap (the hydroxy-bearing ring C atom). In the crystal, molecules are connected via bifurcated O—H⋯(O,O) hydrogen bonds, generating [010] chains.

Related literature

For further synthetic details, see: Abraham et al. (2001 , 2004 ); Brown (1973 ); Evans et al. (1981 , 1999 ); Otera et al. (1992 ). For the structure of the major diastereisomer arising from the same reaction, see: Gille et al. (2008 ).

Experimental

Crystal data

C₁₁H₁₈O₃
M_r = 198.25
Monoclinic, P 2₁
a = 7.7265 (10) Å
b = 6.4798 (8) Å
c = 11.0598 (16) Å
β = 92.563 (14)°
V = 553.17 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.50 × 0.18 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer
Absorption correction: none
3255 measured reflections
1129 independent reflections
737 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.048
S = 0.99
1129 reflections
131 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.84	2.52	3.023 (2)	120
O3—H3⋯O2ⁱ	0.84	2.10	2.931 (3)	171
Symmetry code: (i) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis CCD; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050399/hb5238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050399/hb5238Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was synthesized using a catalytic asymmetric Gosteli-Claisen rearrangement (Abraham et al., 2001; Abraham et al., 2004), a diastereoselective reduction with K-Selectride (Brown, 1973) and an Evans aldol addition (Evans et al., 1981). In order to verify the relative configuration of the obtained diastereomeric aldol adducts, 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2,5,6-trimethyloct-7-enoyl) -4-isopropyloxazolidin-2-one, (III), the γ-lactones (II) and (I) were prepared by removal of the silyl protecting group (Otera et al., 1992) and subsequent in situ lactonization. The diastereomeric mixture of the γ-lactones could be separated by column chromatography. An X-ray crystal structure analysis of the major diastereomer (II) has already been published (Gille et al., 2008). Fig. 1 depicts the structure of the isolated minor diastereomer (I). The configuration of the chiral C atoms in (I) can be attributed to the stereochemical course of the Evans aldol addition (C3 R and C4 R), the diastereoselective reduction with K-Selectride (C5 S) and the catalytic asymmetric Claisen rearrangement (C[2] S and C[3] R) using the chiral Lewis acid [Cu{(S,S)-tert-butyl-box}](H₂O)₂(SbF₆)₂ (Evans et al., 1999).

Related literature top

For further synthetic details, see: Abraham et al. (2001, 2004); Brown (1973); Evans et al. (1981, 1999); Otera et al. (1992). For the structure of the major diastereisomer arising from the same reaction, see: Gille et al. (2008).

Experimental top

The title compound, (I), was synthesized from the corresponding aldol adduct, (III), using tetrabutylammonium fluoride (TBAF) in the presence of acetic acid (Otera et al., 1992) to remove the silyl protecting group. The subsequent lactonization proceeded in situ .

To an ice-cooled solution of crude (III) (dr = 49/51, 0.04 g, 0.10 mmol, 1 eq) in THF (1 ml, 11 ml/mmol III) was added a solution of AcOH (0.5 µl, 0.010 mmol, 0.1 eq) in THF (0.1 ml, 1.1 ml/mmol III) and TBAF (1 M in THF, 0.11 ml, 0.11 mmol, 1.1 eq). After 15 min at 273 K, the reaction mixture was diluted by the addition of saturated aqueous NH₄Cl solution. The aqueous layer was extracted with CH₂Cl₂ (4x) and the combined organic phases were dried (MgSO₄) and concentrated under reduced pressure. Purification by flash chromatography (crude product charged on silica gel, cyclohexane/ethyl acetate 10/1 to 5/1) afforded lactone (I) (0.006 g, 0.03 mmol, 30%) as a single diastereomer and additionally a mixture of (I) and the diastereomer (II) (0.013 g, 0.07 mmol, 69%, dr = 70/30) as colourless crystals. Subsequent recrystallization of (I) by vapor diffusion technique from isohexane and ethyl acetate provided a colourless plate of (I) single-crystal suitable for an X-ray crystal structure analysis. R_f 0.35 (cyclohexane/ethyl acetate 2/1); mp 378 K; ¹H NMR (CDCl₃, 400 MHz, δ): 0.92 (d, ³J = 7.1 Hz, 3H), 1.00 (d, ³J = 7.0 Hz, 3H), 1.32 (d, ³J = 7.2 Hz, 3H), 1.85 (dqd, ³J = 8.2, 7.1, 4.9 Hz, 1H), 2.1 (br. s, 1H), 2.51–2.63 (m, 1H), 2.63 (dq, ³J = 8.4, 7.2 Hz, 1H), 3.92 (dd, ³J = 7.4, 8.2 Hz, 1H), 4.07 (dd, ³J = 8.4, 7.4 Hz, 1H), 5.04 (dd, ³J(E) = 17.8 Hz, ²J = 1.3 Hz, 1H), 5.05 (dd, ³J(Z) = 10.0 Hz, ²J = 1.3 Hz, 1H), 5.81 (ddd, ³J(E) = 17.8 Hz, ³J(Z) = 10.0 Hz, ³J = 6.8 Hz, 1H); ¹³C NMR (CDCl₃, 101 MHz, δ): 10.1 (CH₃), 12.9 (CH₃), 13.7 (CH₃), 37.8 (CH), 41.4 (CH), 44.4 (CH), 78.0 (CH), 84.7 (CH), 114.5 (CH₂), 142.6 (CH), 176.4 (C); IR (cm^-1): 3400(br,s) (ν O—H, OH in H-bridges), 3085(w) (ν C—H, olefin), 2970(s) 2925(s) 2890(m) 2855(m) (ν C—H, CH, CH₃), 1735(s) (ν C=O, lactone), 1640(w) (ν C=C), 1455(m) (δ_as C—H, CH₎, 1380(m) (δ_s C—H, CH₃), 1095(s) (ν C—O, alcohol), 1010(s) 910(s) (δ C—H, olefin); Anal. Calcd. for C₁₁H₁₈O₃: C, 66.6; H, 9.2; Found: C, 66.6; H, 9.4; [α]_D²⁰ +16.0 (c 0.6, CHCl₃); C₁₁H₁₈O₃, M = 198.26 g/mol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. : The molecular structure of (I) with displacement ellipsoids shown at the 30% probability level.

(3R,4R,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3- methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one top

Crystal data top

C₁₁H₁₈O₃	F(000) = 216
M_r = 198.25	D_x = 1.190 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1159 reflections
a = 7.7265 (10) Å	θ = 2.6–29.1°
b = 6.4798 (8) Å	µ = 0.09 mm⁻¹
c = 11.0598 (16) Å	T = 173 K
β = 92.563 (14)°	Plate, colourless
V = 553.17 (13) Å³	0.50 × 0.18 × 0.04 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur S CCD diffractometer	737 reflections with I > 2σ(I)
Radiation source: Enhance (Mo) X-ray Source	R_int = 0.040
Graphite monochromator	θ_max = 25.5°, θ_min = 2.6°
Detector resolution: 16.0560 pixels mm^-1	h = −10→10
ω scans	k = −7→8
3255 measured reflections	l = −14→14
1129 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.048	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.011P)²] where P = (F_o² + 2F_c²)/3
1129 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₁H₁₈O₃	V = 553.17 (13) Å³
M_r = 198.25	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.7265 (10) Å	µ = 0.09 mm⁻¹
b = 6.4798 (8) Å	T = 173 K
c = 11.0598 (16) Å	0.50 × 0.18 × 0.04 mm
β = 92.563 (14)°

Data collection top

Oxford Diffraction Xcalibur S CCD diffractometer	737 reflections with I > 2σ(I)
3255 measured reflections	R_int = 0.040
1129 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	1 restraint
wR(F²) = 0.048	H-atom parameters constrained
S = 0.99	Δρ_max = 0.14 e Å⁻³
1129 reflections	Δρ_min = −0.15 e Å⁻³
131 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.2173 (2)	0.1438 (2)	0.07628 (15)	0.0251 (5)
O2	0.2731 (2)	0.0175 (3)	−0.10413 (17)	0.0328 (6)
O3	0.1599 (2)	0.6838 (3)	0.05289 (17)	0.0370 (6)
H3	0.2032	0.7730	0.0082	0.056*
C1	0.2453 (3)	0.1658 (5)	−0.0428 (2)	0.0267 (8)
C2	0.2329 (4)	0.3900 (4)	−0.0771 (2)	0.0251 (8)
H2	0.1128	0.4168	−0.1109	0.030*
C3	0.2533 (3)	0.4969 (4)	0.0446 (2)	0.0275 (8)
H3A	0.3790	0.5230	0.0645	0.033*
C4	0.1847 (4)	0.3431 (4)	0.1331 (3)	0.0251 (7)
H4	0.0569	0.3630	0.1382	0.030*
C5	0.2674 (4)	0.3375 (4)	0.2598 (2)	0.0293 (8)
H5	0.3954	0.3280	0.2512	0.035*
C6	0.2135 (4)	0.1458 (4)	0.3322 (2)	0.0314 (8)
H6	0.2292	0.0238	0.2784	0.038*
C7	0.3345 (4)	0.1158 (5)	0.4405 (3)	0.0409 (9)
H7	0.4546	0.1147	0.4255	0.049*
C8	0.2950 (4)	0.0912 (5)	0.5523 (2)	0.0487 (10)
H8A	0.1770	0.0910	0.5730	0.058*
H8B	0.3841	0.0735	0.6134	0.058*
C9	0.3607 (3)	0.4531 (4)	−0.1730 (2)	0.0350 (9)
H9A	0.4789	0.4182	−0.1443	0.053*
H9B	0.3523	0.6022	−0.1872	0.053*
H9C	0.3323	0.3793	−0.2487	0.053*
C10	0.2329 (4)	0.5418 (4)	0.3243 (2)	0.0401 (9)
H10A	0.2922	0.6541	0.2836	0.060*
H10B	0.2765	0.5329	0.4087	0.060*
H10C	0.1080	0.5689	0.3218	0.060*
C11	0.0231 (3)	0.1493 (5)	0.3622 (2)	0.0434 (9)
H11A	−0.0082	0.0167	0.3979	0.065*
H11B	−0.0484	0.1728	0.2881	0.065*
H11C	0.0033	0.2605	0.4201	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0324 (13)	0.0134 (13)	0.0295 (11)	−0.0005 (11)	0.0026 (10)	−0.0004 (11)
O2	0.0385 (14)	0.0195 (12)	0.0403 (14)	−0.0003 (11)	0.0013 (11)	−0.0058 (12)
O3	0.0427 (14)	0.0116 (11)	0.0573 (15)	0.0053 (11)	0.0087 (11)	0.0052 (12)
C1	0.0145 (16)	0.0214 (18)	0.044 (2)	−0.0032 (17)	−0.0048 (15)	0.003 (2)
C2	0.0219 (17)	0.0155 (18)	0.038 (2)	−0.0004 (14)	0.0015 (15)	0.0037 (15)
C3	0.0222 (18)	0.0125 (16)	0.048 (2)	0.0004 (16)	0.0007 (16)	0.0048 (16)
C4	0.0229 (17)	0.0143 (16)	0.0380 (19)	0.0038 (15)	0.0020 (15)	−0.0005 (16)
C5	0.0261 (17)	0.0224 (19)	0.039 (2)	0.0040 (16)	−0.0001 (16)	−0.0068 (17)
C6	0.048 (2)	0.0133 (19)	0.0330 (18)	0.0029 (17)	0.0011 (16)	−0.0060 (17)
C7	0.049 (2)	0.038 (2)	0.0359 (17)	0.0078 (19)	0.0001 (17)	0.0032 (18)
C8	0.054 (3)	0.052 (2)	0.039 (2)	−0.003 (2)	−0.005 (2)	0.0019 (19)
C9	0.0337 (19)	0.0271 (19)	0.045 (2)	−0.0014 (17)	0.0090 (16)	0.0070 (17)
C10	0.046 (2)	0.025 (2)	0.049 (2)	−0.0045 (17)	0.0060 (18)	−0.0113 (17)
C11	0.049 (2)	0.037 (2)	0.0442 (19)	−0.010 (2)	0.0005 (17)	0.007 (2)

Geometric parameters (Å, º) top

O1—C1	1.352 (3)	C6—C7	1.499 (3)
O1—C4	1.463 (3)	C6—C11	1.523 (3)
O2—C1	1.201 (3)	C6—H6	1.0000
O3—C3	1.415 (3)	C7—C8	1.296 (3)
O3—H3	0.8400	C7—H7	0.9500
C1—C2	1.504 (4)	C8—H8A	0.9500
C2—C3	1.516 (3)	C8—H8B	0.9500
C2—C9	1.536 (3)	C9—H9A	0.9800
C2—H2	1.0000	C9—H9B	0.9800
C3—C4	1.510 (3)	C9—H9C	0.9800
C3—H3A	1.0000	C10—H10A	0.9800
C4—C5	1.515 (3)	C10—H10B	0.9800
C4—H4	1.0000	C10—H10C	0.9800
C5—C10	1.533 (3)	C11—H11A	0.9800
C5—C6	1.544 (4)	C11—H11B	0.9800
C5—H5	1.0000	C11—H11C	0.9800

C1—O1—C4	111.3 (2)	C7—C6—C5	110.2 (2)
C3—O3—H3	109.5	C11—C6—C5	112.7 (2)
O2—C1—O1	120.4 (3)	C7—C6—H6	106.6
O2—C1—C2	129.9 (2)	C11—C6—H6	106.6
O1—C1—C2	109.7 (3)	C5—C6—H6	106.6
C1—C2—C3	102.4 (2)	C8—C7—C6	127.8 (3)
C1—C2—C9	113.4 (2)	C8—C7—H7	116.1
C3—C2—C9	116.5 (2)	C6—C7—H7	116.1
C1—C2—H2	108.1	C7—C8—H8A	120.0
C3—C2—H2	108.1	C7—C8—H8B	120.0
C9—C2—H2	108.1	H8A—C8—H8B	120.0
O3—C3—C4	109.1 (2)	C2—C9—H9A	109.5
O3—C3—C2	114.6 (2)	C2—C9—H9B	109.5
C4—C3—C2	104.4 (2)	H9A—C9—H9B	109.5
O3—C3—H3A	109.5	C2—C9—H9C	109.5
C4—C3—H3A	109.5	H9A—C9—H9C	109.5
C2—C3—H3A	109.5	H9B—C9—H9C	109.5
O1—C4—C3	103.4 (2)	C5—C10—H10A	109.5
O1—C4—C5	107.6 (2)	C5—C10—H10B	109.5
C3—C4—C5	118.0 (2)	H10A—C10—H10B	109.5
O1—C4—H4	109.1	C5—C10—H10C	109.5
C3—C4—H4	109.1	H10A—C10—H10C	109.5
C5—C4—H4	109.1	H10B—C10—H10C	109.5
C4—C5—C10	109.6 (2)	C6—C11—H11A	109.5
C4—C5—C6	112.7 (2)	C6—C11—H11B	109.5
C10—C5—C6	113.4 (2)	H11A—C11—H11B	109.5
C4—C5—H5	106.9	C6—C11—H11C	109.5
C10—C5—H5	106.9	H11A—C11—H11C	109.5
C6—C5—H5	106.9	H11B—C11—H11C	109.5
C7—C6—C11	113.6 (2)

C4—O1—C1—O2	−179.5 (2)	C2—C3—C4—O1	28.3 (3)
C4—O1—C1—C2	−0.1 (3)	O3—C3—C4—C5	−90.1 (3)
O2—C1—C2—C3	−162.7 (3)	C2—C3—C4—C5	147.0 (2)
O1—C1—C2—C3	18.0 (3)	O1—C4—C5—C10	−178.7 (2)
O2—C1—C2—C9	−36.3 (4)	C3—C4—C5—C10	64.9 (3)
O1—C1—C2—C9	144.4 (2)	O1—C4—C5—C6	−51.4 (3)
C1—C2—C3—O3	−147.4 (2)	C3—C4—C5—C6	−167.8 (2)
C9—C2—C3—O3	88.3 (3)	C4—C5—C6—C7	163.9 (2)
C1—C2—C3—C4	−28.1 (3)	C10—C5—C6—C7	−70.9 (3)
C9—C2—C3—C4	−152.4 (2)	C4—C5—C6—C11	−68.0 (3)
C1—O1—C4—C3	−18.0 (3)	C10—C5—C6—C11	57.3 (3)
C1—O1—C4—C5	−143.6 (2)	C11—C6—C7—C8	0.8 (5)
O3—C3—C4—O1	151.2 (2)	C5—C6—C7—C8	128.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.84	2.52	3.023 (2)	120
O3—H3···O2ⁱ	0.84	2.10	2.931 (3)	171

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₈O₃
M_r	198.25
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	7.7265 (10), 6.4798 (8), 11.0598 (16)
β (°)	92.563 (14)
V (Å³)	553.17 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.18 × 0.04

Data collection
Diffractometer	Oxford Diffraction Xcalibur S CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3255, 1129, 737
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.048, 0.99
No. of reflections	1129
No. of parameters	131
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.84	2.52	3.023 (2)	120
O3—H3···O2ⁱ	0.84	2.10	2.931 (3)	171

Symmetry code: (i) x, y+1, z.

References

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Volume 65| Part 12| December 2009| Page o3274

doi:10.1107/S1600536809050399

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3R,4R,5S)-4-Hydr­­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-di­hydro­furan-2(3H)-one

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Experimental

Crystal data

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Refinement

Supporting information

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organic compounds

(3R,4R,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one