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

Gille, A.; Bläser, D.; Boese, R.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536808042414

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o154

doi:10.1107/S1600536808042414

Open

access

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

Annika Gille,^a Dieter Bläser,^b Roland Boese,^b Hans Preut ^a ^* and Martin Hiersemann ^a

^aFakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany, and ^bFachbereich Chemie, Universität Duisburg-Essen, Campus Essen UniversitätsStrasse 7, 45117 Essen, Germany
^*Correspondence e-mail: hans.preut@udo.edu

(Received 21 November 2008; accepted 12 December 2008; online 17 December 2008)

The relative configuration of the title compound, C₁₁H₁₈O₃, was corroborated by single-crystal X-ray diffraction analysis. In the crystal, molecules are linked via a O—H⋯O hydrogen bond and a chain of molecules is formed along [010].

Related literature

For further synthetic details, see: Abraham, Körner & Hiersemann (2004 ); Abraham, Körner et al. (2004 ); Evans et al. (1981 , 1999 ); Körner & Hiersemann (2006 , 2007 ); Mitsunobu (1981 ); Mitsunobu & Yamada (1967 ); Mitsunobu et al. (1967 ); Otera et al. (1992 ); Pollex & Hiersemann (2005 ).

Experimental

Crystal data

C₁₁H₁₈O₃
M_r = 198.25
Monoclinic, P 2₁
a = 7.604 (2) Å
b = 6.574 (2) Å
c = 11.323 (4) Å
β = 91.211 (7)°
V = 565.9 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 (2) K
0.35 × 0.10 × 0.07 mm

Data collection

Siemens SMART three-axis goniometer with APEXII area-detector diffractometer
Absorption correction: none
7868 measured reflections
1507 independent reflections
1076 reflections with I > 2σ(I)
R_int = 0.131

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.098
S = 0.98
1507 reflections
132 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.84	2.02	2.830 (3)	163
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808042414/hb2861sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042414/hb2861Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was synthesized using a catalytic asymmetric Claisen rearrangement (Abraham, Körner et al., 2004; Abraham, Körner & Hiersemann, 2004; Pollex & Hiersemann, 2005; Körner & Hiersemann, 2006, 2007), a diastereoselective reduction with K-Selectride (Körner & Hiersemann, 2006, 2007), a Mitsunobu reaction (Mitsunobu & Yamada, 1967; Mitsunobu et al., 1967; Mitsunobu, 1981) and an Evans aldol addition (Evans et al., 1981). In order to verify the relative configuration of the obtained aldol adduct, 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2,5,6-trimethyloct-7-enoyl)-4-isopropyloxazolidin-2-one, (II), a γ-lactone, (I), was prepared by removal of the silyl protecting group (Otera et al., 1992) and subsequent in situ lactonization. Fig. 1 depicts the structure of the isolated diastereomer (I). The configuration of the chiral C atoms in (I) can be attributed to the stereochemical course of the Evans aldol addition (C3 S and C4 S), the diastereoselective reduction with K-Selectride (C5 S) followed by Mitsunobu reaction (C5 R), 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).

In the crystal, an O—H···O hydrogen bond (Table 1) links the molecules into chains propagating in [010].

Related literature top

For further synthetic details, see: Abraham, Körner & Hiersemann (2004); Abraham, Körner et al. (2004); Evans et al. (1981, 1999); Körner & Hiersemann (2006, 2007); Mitsunobu (1981); Mitsunobu & Yamada (1967); Mitsunobu et al. (1967); Otera et al. (1992); Pollex & Hiersemann (2005).

Experimental top

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

To a solution of diastereomerically pure (II) (66 mg, 0.15 mmol, 1.0 eq) in tetrahydrofuran (0.8 ml) was added acetic acid (0.9 µl, 0.015 mmol, 0.1 eq) in tetrahydrofuran (0.1 ml) and TBAF (1 M in tetrahydrofuran, 0.225 ml, 1.5 eq) at 273 K. After stirring for 20 min at 273 K, the mixture was allowed to warm to room temperature. After stirring the reaction mixture for 4.5 h at room temperature, the reaction was quenched by the addition of sat. aqueous NH₄Cl solution. The phases were separated, and the aqueous phase was extracted with CH₂Cl₂ (3 × 5 ml). The combined organic layers were dried (MgSO₄) and concentrated under reduced pressure. Flash chromatography (isohexane/ethyl acetate 20/1 to 10/1 to 5/1) afforded (I) as a single diastereomer in quantitative yield (29.6 mg, 0.15 mmol) as colourless crystals. Colourless needles of (I) were obtained by vapor diffusion recrystallization technique from isohexane and ethyl acetate: mp 361 K; R_f 0.35 (cyclohexane/ethyl acetate 2/1); ¹H NMR (CDCl₃, 400 MHz, δ): 0.92 (d, J = 6.8 Hz, 3H), 1.05 (d, J = 6.8 Hz, 3H), 1.31 (d, J = 7.1 Hz, 3H), 1.73 (dqd, J = 6.8, 6.8, 3.6 Hz, 1H), 2.14 (br. s, 1 H), 2.33 (apparent sex, J = 7.7 Hz, 1H), 2.59 (dq, J = 8.6, 7.1 Hz, 1H), 3.91 (dd, J = 8.6 Hz, 1H), 4.20 (dd, J = 8.6, 3.6 Hz, 1H), 5.04 (d, ³J(Z) = 10.0 Hz, 1H), 5.05 (d, ³J(E) = 17.8 Hz, 1H), 5.73 (ddd, ³J(E) = 17.8 Hz, ³J(Z) = 10.0 Hz, ³J = 7.7 Hz, 1H); ¹³C NMR (CDCl₃, 100 MHz, δ): 10.7 (CH₃), 12.8 (CH₃), 17.2 (CH₃), 39.4 (CH), 41.0 (CH), 44.2 (CH), 77.2 (CH), 85.2 (CH), 115.1 (CH₂), 143.0 (CH), 176.7 (C); IR (cm^-1): 3405(br,s) (ν O—H, OH in H-bridges), 3090(w) 3005(w) (ν C—H, olefin), 2965(s) 2935(m) 2900(m) 2855(w) (ν_as,s C—H, CH₂, CH₃, CH), 1740(s) (ν C=O, lactone), 1640(w) (ν C=C), 1460(s) (δ_as C—H, CH₃, CH₂), 1380(s) (δ_s C—H, CH₃); Anal. Calcd. for C₁₁H₁₈O₃: C, 66.6; H, 9.2; Found: C, 66.7; H, 9.3; [α]_D²⁰ +61.4 (c 0.487, CHCl₃).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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, 2003).

Figures top

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

(3S,4S,5R)-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 = 1.163 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1365 reflections
a = 7.604 (2) Å	θ = 2.7–26.3°
b = 6.574 (2) Å	µ = 0.08 mm⁻¹
c = 11.323 (4) Å	T = 173 K
β = 91.211 (7)°	Needle, colourless
V = 565.9 (3) Å³	0.35 × 0.10 × 0.07 mm
Z = 2

Data collection top

Siemens SMART three-axis goniometer with APEXII area-detector system diffractometer	1076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.131
Graphite monochromator	θ_max = 28.3°, θ_min = 1.8°
Detector resolution: 512 pixels mm^-1	h = −9→10
Data collection strategy APEX 2/COSMO scans	k = −8→8
7868 measured reflections	l = −15→14
1507 independent reflections

Refinement top

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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0279P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
1507 reflections	Δρ_max = 0.19 e Å⁻³
132 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.077 (11)

Crystal data top

C₁₁H₁₈O₃	V = 565.9 (3) Å³
M_r = 198.25	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.604 (2) Å	µ = 0.08 mm⁻¹
b = 6.574 (2) Å	T = 173 K
c = 11.323 (4) Å	0.35 × 0.10 × 0.07 mm
β = 91.211 (7)°

Data collection top

Siemens SMART three-axis goniometer with APEXII area-detector system diffractometer	1076 reflections with I > 2σ(I)
7868 measured reflections	R_int = 0.131
1507 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	1 restraint
wR(F²) = 0.098	H-atom parameters constrained
S = 0.98	Δρ_max = 0.19 e Å⁻³
1507 reflections	Δρ_min = −0.19 e Å⁻³
132 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	0.2255 (2)	0.2085 (3)	0.91883 (16)	0.0351 (5)
O2	0.1493 (2)	0.7353 (3)	0.96072 (16)	0.0382 (5)
H2	0.2076	0.8318	0.9904	0.057*
O3	0.2839 (2)	0.0670 (3)	1.09375 (17)	0.0408 (5)
C1	0.3186 (5)	0.7143 (7)	0.4846 (3)	0.0700 (11)
H1A	0.1994	0.7345	0.4607	0.084*
H1B	0.4096	0.7302	0.4292	0.084*
C2	0.3570 (4)	0.6651 (5)	0.5929 (3)	0.0471 (8)
H2A	0.4783	0.6469	0.6118	0.057*
C3	0.2316 (4)	0.6337 (4)	0.6919 (2)	0.0381 (7)
H3	0.2615	0.7378	0.7535	0.046*
C4	0.2658 (4)	0.4224 (4)	0.7492 (2)	0.0352 (7)
H4	0.3959	0.4082	0.7615	0.042*
C5	0.1827 (3)	0.4084 (4)	0.8699 (2)	0.0305 (6)
H5	0.0522	0.4226	0.8610	0.037*
C6	0.2512 (3)	0.5554 (4)	0.9651 (2)	0.0309 (6)
H6	0.3778	0.5877	0.9522	0.037*
C7	0.2319 (4)	0.4339 (4)	1.0786 (2)	0.0324 (6)
H7	0.1086	0.4522	1.1059	0.039*
C8	0.2500 (3)	0.2207 (4)	1.0367 (2)	0.0327 (6)
C9	0.0401 (4)	0.6683 (5)	0.6558 (3)	0.0513 (8)
H9A	0.0246	0.8089	0.6288	0.077*
H9B	−0.0348	0.6434	0.7236	0.077*
H9C	0.0072	0.5748	0.5916	0.077*
C10	0.2046 (4)	0.2460 (5)	0.6698 (3)	0.0468 (8)
H10A	0.2487	0.1173	0.7025	0.070*
H10B	0.2503	0.2650	0.5902	0.070*
H10C	0.0758	0.2429	0.6657	0.070*
C11	0.3561 (4)	0.4916 (5)	1.1806 (3)	0.0477 (8)
H11A	0.3352	0.4020	1.2481	0.071*
H11B	0.3347	0.6331	1.2035	0.071*
H11C	0.4781	0.4767	1.1558	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0416 (11)	0.0232 (11)	0.0406 (11)	0.0024 (9)	0.0034 (8)	−0.0022 (8)
O2	0.0413 (11)	0.0230 (10)	0.0504 (12)	0.0052 (9)	0.0008 (9)	−0.0046 (9)
O3	0.0428 (12)	0.0276 (11)	0.0520 (13)	0.0029 (9)	0.0009 (10)	0.0033 (9)
C1	0.078 (2)	0.083 (3)	0.050 (2)	−0.008 (2)	0.0124 (17)	0.006 (2)
C2	0.0516 (19)	0.0459 (19)	0.0439 (19)	−0.0065 (15)	0.0038 (15)	−0.0007 (14)
C3	0.0457 (18)	0.0296 (15)	0.0391 (17)	−0.0013 (13)	0.0026 (14)	−0.0019 (12)
C4	0.0367 (16)	0.0273 (15)	0.0418 (16)	0.0022 (13)	0.0027 (12)	−0.0043 (13)
C5	0.0327 (14)	0.0184 (13)	0.0403 (16)	−0.0005 (12)	0.0005 (12)	−0.0025 (12)
C6	0.0294 (15)	0.0194 (14)	0.0441 (16)	−0.0010 (11)	0.0024 (12)	−0.0012 (12)
C7	0.0328 (15)	0.0250 (14)	0.0396 (16)	−0.0016 (12)	0.0010 (12)	−0.0060 (12)
C8	0.0275 (14)	0.0268 (14)	0.0440 (17)	−0.0030 (12)	0.0027 (12)	−0.0020 (14)
C9	0.057 (2)	0.0446 (19)	0.0527 (19)	0.0102 (16)	0.0027 (15)	0.0093 (14)
C10	0.066 (2)	0.0294 (16)	0.0447 (17)	0.0034 (16)	−0.0029 (15)	−0.0096 (14)
C11	0.054 (2)	0.0397 (17)	0.0489 (19)	−0.0075 (15)	−0.0091 (15)	0.0000 (14)

Geometric parameters (Å, º) top

O1—C8	1.347 (3)	C5—C6	1.531 (4)
O1—C5	1.460 (3)	C5—H5	1.0000
O2—C6	1.414 (3)	C6—C7	1.522 (4)
O2—H2	0.8400	C6—H6	1.0000
O3—C8	1.223 (3)	C7—C8	1.487 (4)
C1—C2	1.296 (4)	C7—C11	1.524 (4)
C1—H1A	0.9500	C7—H7	1.0000
C1—H1B	0.9500	C9—H9A	0.9800
C2—C3	1.501 (4)	C9—H9B	0.9800
C2—H2A	0.9500	C9—H9C	0.9800
C3—C9	1.521 (4)	C10—H10A	0.9800
C3—C4	1.553 (4)	C10—H10B	0.9800
C3—H3	1.0000	C10—H10C	0.9800
C4—C5	1.520 (4)	C11—H11A	0.9800
C4—C10	1.534 (4)	C11—H11B	0.9800
C4—H4	1.0000	C11—H11C	0.9800

C8—O1—C5	110.4 (2)	C7—C6—H6	110.2
C6—O2—H2	109.5	C5—C6—H6	110.2
C2—C1—H1A	120.0	C8—C7—C6	102.4 (2)
C2—C1—H1B	120.0	C8—C7—C11	114.6 (2)
H1A—C1—H1B	120.0	C6—C7—C11	116.1 (2)
C1—C2—C3	127.4 (3)	C8—C7—H7	107.8
C1—C2—H2A	116.3	C6—C7—H7	107.8
C3—C2—H2A	116.3	C11—C7—H7	107.8
C2—C3—C9	113.5 (2)	O3—C8—O1	119.8 (3)
C2—C3—C4	109.4 (2)	O3—C8—C7	129.1 (2)
C9—C3—C4	113.4 (2)	O1—C8—C7	111.1 (2)
C2—C3—H3	106.7	C3—C9—H9A	109.5
C9—C3—H3	106.7	C3—C9—H9B	109.5
C4—C3—H3	106.7	H9A—C9—H9B	109.5
C5—C4—C10	110.8 (2)	C3—C9—H9C	109.5
C5—C4—C3	111.1 (2)	H9A—C9—H9C	109.5
C10—C4—C3	112.7 (2)	H9B—C9—H9C	109.5
C5—C4—H4	107.3	C4—C10—H10A	109.5
C10—C4—H4	107.3	C4—C10—H10B	109.5
C3—C4—H4	107.3	H10A—C10—H10B	109.5
O1—C5—C4	107.56 (19)	C4—C10—H10C	109.5
O1—C5—C6	103.3 (2)	H10A—C10—H10C	109.5
C4—C5—C6	117.0 (2)	H10B—C10—H10C	109.5
O1—C5—H5	109.5	C7—C11—H11A	109.5
C4—C5—H5	109.5	C7—C11—H11B	109.5
C6—C5—H5	109.5	H11A—C11—H11B	109.5
O2—C6—C7	113.9 (2)	C7—C11—H11C	109.5
O2—C6—C5	109.0 (2)	H11A—C11—H11C	109.5
C7—C6—C5	103.1 (2)	H11B—C11—H11C	109.5
O2—C6—H6	110.2

C1—C2—C3—C9	−0.8 (5)	C4—C5—C6—O2	90.6 (3)
C1—C2—C3—C4	126.9 (4)	O1—C5—C6—C7	−30.1 (2)
C2—C3—C4—C5	163.2 (2)	C4—C5—C6—C7	−148.1 (2)
C9—C3—C4—C5	−69.1 (3)	O2—C6—C7—C8	146.5 (2)
C2—C3—C4—C10	−71.8 (3)	C5—C6—C7—C8	28.6 (3)
C9—C3—C4—C10	55.9 (3)	O2—C6—C7—C11	−88.0 (3)
C8—O1—C5—C4	144.9 (2)	C5—C6—C7—C11	154.1 (2)
C8—O1—C5—C6	20.6 (2)	C5—O1—C8—O3	178.6 (2)
C10—C4—C5—O1	55.7 (3)	C5—O1—C8—C7	−2.0 (3)
C3—C4—C5—O1	−178.3 (2)	C6—C7—C8—O3	161.8 (3)
C10—C4—C5—C6	171.3 (2)	C11—C7—C8—O3	35.3 (4)
C3—C4—C5—C6	−62.6 (3)	C6—C7—C8—O1	−17.5 (3)
O1—C5—C6—O2	−151.49 (19)	C11—C7—C8—O1	−144.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.84	2.02	2.830 (3)	163

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)	7.604 (2), 6.574 (2), 11.323 (4)
β (°)	91.211 (7)
V (Å³)	565.9 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.10 × 0.07

Data collection
Diffractometer	Siemens SMART three-axis goniometer with APEXII area-detector system diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7868, 1507, 1076
R_int	0.131
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.098, 0.98
No. of reflections	1507
No. of parameters	132
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.19

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.84	2.02	2.830 (3)	163

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

References

Abraham, L., Körner, M. & Hiersemann, M. (2004). Tetrahedron Lett. 45, 3647–3650. Web of Science CrossRef CAS Google Scholar
Abraham, L., Körner, M., Schwab, P. & Hiersemann, M. (2004). Adv. Synth. Catal. 346, 1281–1294. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Evans, D. A., Bartroli, J. & Shih, T. L. (1981). J. Am. Chem. Soc. 103, 2127–2129. CrossRef CAS Web of Science Google Scholar
Evans, D. A., Miller, S. J., Lectka, T. & Matt, V. P. (1999). J. Am. Chem. Soc. 121, 7559–7573. Web of Science CrossRef CAS Google Scholar
Körner, M. & Hiersemann, M. (2006). Synlett, pp. 121–123. Google Scholar
Körner, M. & Hiersemann, M. (2007). Org. Lett. 9, 4979–4982. Web of Science PubMed Google Scholar
Mitsunobu, O. (1981). Synthesis, pp. 1–28. CrossRef Web of Science Google Scholar
Mitsunobu, O. & Yamada, M. (1967). Bull. Chem. Soc. Jpn, 40, 2380–2382. CrossRef CAS Web of Science Google Scholar
Mitsunobu, O., Yamada, M. & Mukaiyama, T. (1967). Bull. Chem. Soc. Jpn, 40, 935–939. CrossRef CAS Web of Science Google Scholar
Otera, J., Niibo, Y. & Nozaki, H. (1992). Tetrahedron Lett. 33, 3655–3658. CrossRef CAS Web of Science Google Scholar
Pollex, A. & Hiersemann, M. (2005). Org. Lett. 7, 5705–5708. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o154

doi:10.1107/S1600536808042414

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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