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Communication

Synthesis of Novel Spiro-Isoxazolidine Derivatives of 9α-Hydroxyparthenolide

by
Mohamed Zaki
1,*,
Mohammed Loubidi
2 and
Sabine Berteina-Raboin
2,*
1
Laboratoire Interdisciplinaire de Modélisation, Simulation et Innovation Scientifique (LIMSIS), Département de Sciences, Ecole Normale Supérieure, Moulay Ismail University, BP 3104, Toulal 50000, Meknès, Marocco
2
Institut de Chimie Organique et Analytique (ICOA), Université d’Orléans, UMR-CNRS 7311, BP 6759, Rue de Chartres, CEDEX 2, 45067 Orléans, France
*
Authors to whom correspondence should be addressed.
Molbank 2025, 2025(3), M2054; https://doi.org/10.3390/M2054
Submission received: 4 July 2025 / Revised: 22 August 2025 / Accepted: 25 August 2025 / Published: 28 August 2025
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Abstract

The 1,3-dipolar cycloaddition reaction was applied to 9α-hydroxyparthenolide, an important sesquiterpene component of Anvillea radiata that was extracted directly from plant material collected in Morocco. Several new spiro-isoxazolidine derivatives were generated on the B-ring of 9α-hydroxyparthenolide (α-methylene-γ-butyrolactone (1)) by 1,3-dipolar cycloaddition of its exocyclic double bond with various nitrones. These compounds were fully characterized by spectroscopic methods.

1. Introduction

Plants have been an integral part of the healthcare industry for centuries and form the basis of many traditional and modern pharmaceutical remedies. They contain a wide range of bioactive compounds that can be used to treat a variety of ailments [1]. The study of medicinal plants has led to the discovery of essential medicines such as aspirin, derived from willow bark [2].
Sesquiterpene lactones are a class of natural compounds found in various plants, particularly in the Asteraceae family [3,4]. These types of derivatives are of significant importance in medicine due to their diverse biological activities and have candidates in various phases of clinical trials such as parthenolide, costunolide, helenalin, and artemisinin (Figure 1) [5,6,7]. Parthenolide (2) is a sesquiterpene lactone originally purified from feverfew shoots [8]. It is used in the treatment of fever, migraines, and rheumatoid arthritis and as an anti-inflammatory agent [9,10,11]. It has shown powerful anticancer activity [12,13].
As part of the Moroccan plant development program [14,15,16], Anvillea radiata, an invasive perennial weed, has been particularly studied. Easily accessible, it constitutes a renewable source of sesquiterpene lactones such as 9α-hydroxyparthenolide [16]. This molecule is directly isolated with good yield from the aerial part of the plant (Figure 2) [16,17].
Here we propose the introduction of an isoxazolidine functionality to form libraries of structurally original spiro-bicyclic analogs of 9α-hydroxyparthenolide (1) by 1,3-dipolar cycloaddition of several nitrones onto the exocyclic double bond of the B-ring of 9α-hydroxyparthenolide. The numbering system commonly used for this structure is shown in Figure 3.

2. Results and Discussion

Spiro-isoxazolidine derivatives of 9α-hydroxyparthenolide were successfully synthesized by a 1,3-dipolar cycloaddition reaction using various 3a–h nitrones. These nitrones 3a–h were obtained according to the procedure previously reported in the literature. This involves reducing nitroaryls in the presence of zinc and acetic acid to give the corresponding arylhydroxylamines. These were then condensed with various aromatic aldehydes [18].
In order to optimize reaction conditions, initial tests were carried out with nitrone 3b by adjusting various experimental parameters, including the solvent, nitrone quantity, and reaction time. The results are summarized in Table 1.
When the reaction was carried out under the same conditions as those reported in the literature, using dry toluene refluxed for 6 h, the desired product was obtained in only 10% yield [19]. Under these conditions, most of the starting material was recovered. Increasing the reaction time and the amount of nitrone (2 equiv.) had little effect on yield and conversion. In view of this modest result, toluene was replaced by benzene, giving the desired product in a much higher yield (76%). A comparable result was obtained using 1.5 equiv. of nitrone instead of 1.1 equiv.
The optimized conditions were extended to various nitrones and the spiro-isoxazolidine derivatives 4a–h were isolated in satisfactory yields as two diastereomers (50:50) after purification by flash chromatography (Scheme 1). The diastereomers were not separated by flash chromatography. This 1,3-dipolar cycloaddition reaction is regiospecific but not stereoselective.
The operating conditions tolerate various aryl-containing nitrones with electron-donating (CH3, OCH3) or electron-withdrawing substituents (CF3, F). Heteroaryl-substituted nitrones were also successfully used under these conditions. The reaction sequence was also successfully applied to N-alkyl-substituted aryl derivatives, with an isolated yield of 62% in the case of the dimethylamine substrate.
The synthesized spiro-isoxazolidines were fully characterized by 1H and 13C NMR spectroscopic techniques, see 1H and 13C NMR spectra of compounds 4a to 4h and 2D MDL molfile in Supplementary Materials. The formation of the spiro-isoxazoline ring was clearly confirmed by the disappearance of the alkene protons adjacent to the lactone ring and the appearance of the benzyl proton adjacent to the nitrogen atom in the isoxazolidine ring, as well as the appearance of the aromatic proton. The CH chemical shift in the asymmetric center generated is generally between 5.46 and 5.63 ppm. For example, in the case of product 4b, which enabled us to optimize the reaction, the signal corresponding to the CH proton of the asymmetric center appears at 5.63 ppm.

3. Materials and Methods

All reagents were purchased from commercial suppliers and were used without further purification. The reactions were monitored by thin-layer chromatography (TLC) analysis using silica gel (60 F254) plates. Compounds were visualized by UV irradiation. Flash column chromatography was performed on silica gel 60 (230–400 mesh, 0.040–0.063 mm). 1H and 13C NMR spectra were recorded on a Bruker AVANCE II spectrometer (Billerica, MA, USA) at 250 MHz (13C, 62.9 MHz) and on a Bruker AVANCE III HD nanobay (Billerica, MA, USA) at 400 MHz (13C 101 MHz). Chemical shifts are given in parts per million from tetramethylsilane (TMS) as an internal standard, in deuterated solvent (CDCl3). The following abbreviations were used for the proton spectra multiplicities: b: broad, s: singlet, d: doublet, t: triplet, q: quartet, p: pentuplet, m: multiplet. Coupling constants (J) are reported in hertz (Hz). High-resolution mass spectra (HRMS (ESI)) were performed on a Maxis Bruker 4G (Billerica, MA, USA).

3.1. General Procedure for the Synthesis of Spiro-Isoxazolidines

A solution of 9α-hydroxyparthenolide (100 mg, 1 equiv.) in benzene (2 mL) was treated with the appropriate nitrone (1.1 equiv.). The resulting suspension was refluxed for 12 h, concentrated under reduced pressure, and purified by flash chromatography (silica gel) to afford the desired spiro-isoxazolidine.

3.1.1. Compound 4a: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-5′-Hydroxy-6′,9a′-dimethyl-2,3-diphenyl-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno [2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.56 petroleum ether/ethyl acetate 6/4) provided 4a (80%) as a yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.52–7.45 (m, 2H), 7.37–7.27 (m, 3H), 7.20–7.11 (m, 2H), 7.03–6.95 (m, 3H), 5.62 (ddt, J = 12.6, 4.0, 1.8 Hz, 1H), 4.33–4.26 (m, 2H), 3.78 (t, J = 9.5 Hz, 1H), 3.18 (t, J = 9.5 Hz, 1H), 2.99 (dd, J = 13.1, 7.9 Hz, 1H), 2.74 (d, J = 9.0 Hz, 1H), 2.57–2.39 (m, 2H), 2.33 (dd, J = 14.5, 6.8 Hz, 1H), 2.28–2.21 (m, 1H), 2.16 (ddd, J = 13.0, 5.5, 2.0 Hz, 1H), 1.89 (dd, J = 14.6, 9.3 Hz, 1H), 1.84–1.80 (m, 1H), 1.70 (s, 3H), 1.62 (s, 1H), 1.28 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 175.14, 149.25, 139.21, 136.84, 129.36, 128.77, 127.96, 124.12, 122.37, 118.69, 83.10, 79.88, 71.06, 70.75, 66.73, 61.80, 44.64, 39.58, 37.00, 31.68, 23.68, 17.43, 16.63. HRMS (ESI+): m/z [M + H]+ Calcd. for C28H32NO5: 462.2275; found 462.2276.

3.1.2. Compound 4b: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-5′-Hydroxy-3-(4-methoxyphenyl)-6′,9a′-dimethyl-2-phenyl-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno[2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.48 petroleum ether/ethyl acetate 6/4) provided 4b (76%) as a colorless oil; 1H NMR (400 MHz, CDCl3) δ 7.33 (d, J = 8.4 Hz, 2H), 7.19–7.10 (m, 4H), 7.01 (t, J = 7.1 Hz, 1H), 6.88 (d, J = 8.4 Hz, 2H), 5.63 (dd, J = 13.0, 3.8 Hz, 1H), 4.72 (dd, J = 10.9, 5.8 Hz, 1H), 4.38 (d, J = 6.4 Hz, 1H), 3.80 (s, 3H), 3.28 (t, J = 9.9 Hz, 1H), 2.81–2.72 (m, 2H), 2.68 (d, J = 11.4 Hz, 1H), 2.51 (dtd, J = 47.9, 12.7, 5.5 Hz, 3H), 2.31–2.11 (m, 3H), 2.01 (s, 1H), 1.85 (dd, J = 14.6, 9.8 Hz, 1H), 1.69 (s, 3H), 1.28 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 174.82, 159.73, 150.31, 136.34, 129.91, 128.65, 128.55, 124.39, 122.18, 119.20, 114.48, 83.97, 79.71, 70.88, 69.68, 66.41, 61.68, 55.44, 43.87, 39.06, 36.86, 31.87, 23.52, 17.23, 16.33.

3.1.3. Compound 4c: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-5′-Hydroxy-3-(4-methoxyphenyl)-6′,9a′-dimethyl-2-(p-tolyl)-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno[2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.62 petroleum ether/ethyl acetate 6/4) provided 4c (78%) as a yellowish oil; 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J = 8.7 Hz, 2H), 6.98–6.93 (m, 2H), 6.87 (dd, J = 11.2, 8.6 Hz, 4H), 5.56 (dd, J = 12.5, 3.7 Hz, 1H), 4.79 (dd, J = 10.6, 6.3 Hz, 1H), 4.36 (d, J = 6.6 Hz, 1H), 4.17 (t, J = 9.3 Hz, 1H), 3.80 (s, 3H), 2.97 (dd, J = 12.9, 6.3 Hz, 1H), 2.82 (t, J = 8.6 Hz, 1H), 2.72–2.57 (m, 2H), 2.49 (dd, J = 13.0, 5.4 Hz, 1H), 2.23 (s, 3H), 2.17 (ddd, J = 12.9, 5.6, 1.9 Hz, 1H), 1.95 (dd, J = 15.8, 8.0 Hz, 1H), 1.72 (d, J = 1.2 Hz, 3H), 1.69–1.50 (m, 2H), 1.30 (s, 3H), 1.28–1.14 (m, 2H); 13C NMR (101 MHz, CDCl3) δ 174.22, 159.36, 147.53, 138.21, 134.00, 130.61, 129.15, 128.52, 121.21, 118.78, 114.18, 84.24, 82.91, 70.83, 70.75, 66.76, 61.31, 55.28, 44.95, 40.01, 36.76, 29.69, 23.32, 20.77, 17.09, 16.43. HRMS (ESI+): m/z [M + H]+ Calcd. for C30H36NO6: 506.2537; found 506.2538.

3.1.4. Compound 4d: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-2-(4-fluorophenyl)-5′-Hydroxy-6′,9a′-dimethyl-3-(p-tolyl)-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno[2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.29 petroleum ether/ethyl acetate 5/5) provided 4d (66%) as a colorless oil; 1H NMR (400 MHz, CDCl3) δ 7.33–7.29 (m, 2H), 7.12 (d, J = 7.7 Hz, 2H), 6.99 (ddd, J = 6.8, 4.7, 2.4 Hz, 2H), 6.83 (td, J = 8.7, 1.9 Hz, 2H), 5.63–5.56 (m, 1H), 4.34 (d, J = 6.4 Hz, 1H), 4.11 (t, J = 8.7 Hz, 1H), 3.81–3.74 (m, 1H), 3.15 (t, J = 9.5 Hz, 1H), 2.92 (dd, J = 13.2, 7.4 Hz, 1H), 2.71 (dd, J = 9.1, 1.7 Hz, 1H), 2.54–2.36 (m, 3H), 2.35–2.31 (m, 3H), 2.24 (d, J = 13.2 Hz, 1H), 2.18–2.10 (m, 1H), 2.06–1.98 (m, 1H), 1.90 (dd, J = 14.5, 9.4 Hz, 1H), 1.70 (s, 3H), 1.27 (d, J = 1.7 Hz, 4H); 13C NMR (101 MHz, CDCl3) δ 175.17, 160.97, 158.55, 144.80, 144.78, 138.30, 136.80, 134.69, 129.68, 127.80, 121.96, 121.09, 121.01, 115.14, 114.92, 82.61, 79.60, 71.41, 70.75, 66.45, 61.53, 44.09, 39.18, 36.67, 31.24, 23.34, 21.17, 17.09, 16.31. HRMS (ESI+): m/z [M + H]+ Calcd. for C29H33FNO5: 494.2337; found 494.2340.

3.1.5. Compound 4e: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-5′-Hydroxy-6′,9a′-dimethyl-2-phenyl-3-(4-(trifluoromethyl)phenyl)-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno[2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.18 petroleum ether/ethyl acetate 5/5) provided 4e (62%) as a yellowish oil; 1H NMR (400 MHz, CDCl3) δ 7.74 (d, J = 8.0 Hz, 2H), 7.62 (d, J = 8.0 Hz, 2H), 7.17 (t, J = 7.8 Hz, 2H), 7.03 (t, J = 7.4 Hz, 1H), 6.90 (d, J = 8.0 Hz, 2H), 5.61–5.54 (m, 1H), 4.31 (t, J = 8.7 Hz, 2H), 4.17 (t, J = 9.3 Hz, 1H), 2.91 (dd, J = 11.5, 8.6 Hz, 3H), 2.64 (d, J = 9.3 Hz, 1H), 2.54–2.35 (m, 2H), 2.30–2.14 (m, 2H), 1.89 (dd, J = 15.8, 8.3 Hz, 1H), 1.73 (s, 4H), 1.57 (s, 1H), 1.32 (s, 3H). 13C NMR (101 MHz, CDCl3) δ 173.73, 148.18, 143.79, 137.95, 130.62, 130.30, 128.74, 128.53, 126.06, 126.02, 124.77, 121.69, 119.18, 83.53, 81.96, 70.92, 70.41, 66.97, 61.44, 43.66, 40.09, 36.93, 30.25, 29.85, 23.47, 17.25, 16.58. HRMS (ESI+): m/z [M + H]+ Calcd. for C29H31F3NO5: 530.2149; found 530.2150.

3.1.6. Compound 4f: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-3-(furan-2-yl)-5′-Hydroxy-6′,9a′-dimethyl-2-phenyl-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno[2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.81 petroleum ether/ethyl acetate 3/7) provided 4f (66%) as a yellowish oil; 1H NMR (400 MHz, CDCl3) δ 7.46 (s, 1H), 7.27–7.16 (m, 3H), 7.07–6.92 (m, 3H), 6.41–6.23 (m, 1H), 5.63–5.52 (m, 1H), 4.98 (t, J = 8.3 Hz, 1H), 4.35 (d, J = 6.8 Hz, 1H), 4.20 (t, J = 9.2 Hz, 1H), 2.91 (dt, J = 16.3, 7.7 Hz, 3H), 2.63 (dd, J = 16.9, 7.9 Hz, 2H), 2.48 (td, J = 12.8, 5.3 Hz, 1H), 2.37–2.13 (m, 2H), 2.06–1.86 (m, 1H), 1.72 (s, 3H), 1.68–1.43 (m, 2H), 1.29 (d, J = 23.3 Hz, 3H). 13C NMR (101 MHz, CDCl3) δ 173.85, 150.68, 150.00, 142.89, 138.11, 128.64, 124.18, 121.24, 117.62, 110.48, 108.90, 84.80, 82.92, 70.76, 66.71, 64.94, 61.34, 39.86, 39.74, 36.77, 29.69, 29.52, 23.31, 17.09, 16.38.

3.1.7. Compound 4g: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-5′-Hydroxy-6′,9a′-dimethyl-2-phenyl-3-(thiophen-3-yl)-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno[2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.75 petroleum ether/ethyl acetate 3/7) provided 4g (68%) as a colorless oil; 1H NMR (400 MHz, CDCl3) δ 7.32 (dd, J = 5.1, 2.8 Hz, 1H), 7.25–7.15 (m, 4H), 7.01 (d, J = 7.9 Hz, 3H), 5.66–5.57 (m, 1H), 4.44 (t, J = 8.3 Hz, 1H), 4.29 (d, J = 6.5 Hz, 1H), 3.78 (t, J = 9.4 Hz, 1H), 3.19 (t, J = 9.6 Hz, 1H), 2.93 (dd, J = 13.0, 7.7 Hz, 1H), 2.74 (d, J = 8.9 Hz, 1H), 2.58–2.40 (m, 1H), 2.38–2.09 (m, 2H), 1.92–1.76 (m, 2H), 1.70 (s, 3H), 1.64–1.33 (m, 2H), 1.28 (s, 4H); 13C NMR (101 MHz, CDCl3) δ 174.71, 148.83, 139.40, 136.55, 128.45, 126.87, 126.51, 123.99, 123.22, 122.05, 118.44, 82.75, 79.55, 70.75, 66.40, 66.32, 61.45, 42.95, 39.37, 36.67, 31.36, 23.34, 17.10, 16.30.

3.1.8. Compound 4h: (3a′R,5S,5′R,9a′R,10a′S,10b′S,E)-3-(4-(dimethylamino)phenyl)-5′-Hydroxy-6′,9a′-dimethyl-2-phenyl-3a′,4′,5′,8′,9′,9a′,10a′,10b′-octahydro-2′H-spiro[isoxazolidine-5,3′-oxireno[2′,3′:9,10]cyclodeca[1,2-b]furan]-2′-one

Following the general procedure. Column chromatography on silica gel (Rf = 0.62 petroleum ether/ethyl acetate 2/8) provided 4h (62%) as a brown oil; 1H NMR (250 MHz, CDCl3) δ 7.47–7.34 (m, 2H), 7.34–7.21 (m, 2H), 7.19–6.82 (m, 3H), 6.76–6.58 (m, 2H), 5.63–5.46 (m, 1H), 4.35–4.01 (m, 3H), 3.86–3.64 (m, 1H), 3.12 (t, J = 9.5 Hz, 1H), 3.02–2.77 (m, 8H), 2.77–1.77 (m, 6H), 1.66 (d, J = 3.7 Hz, 4H), 1.34–1.18 (m, 3H). 13C NMR (63 MHz, CDCl3) δ 174.50, 149.95, 148.97, 136.62, 128.72, 128.36, 123.38, 121.72, 118.11, 112.45, 82.53, 79.55, 70.82, 70.71, 67.10, 66.42, 61.33, 44.10, 40.44, 39.25, 36.74, 31.23, 29.61, 23.30, 17.14, 16.29. HRMS (ESI+): m/z [M + H]+ Calcd. for C30H37N2O5: 505.2697; found 505.2698.

4. Conclusions

Here, we present the synthesis of spiro-isoxazolidine derivatives from naturally occurring 9α-hydroxyparthenolide via 1,3-dipolar cycloaddition. Using a plant-extracted chiral starting synthon, this method takes advantage of the substrate’s inherent chirality to efficiently build a new library of spiro-isoxazolidine derivatives. In this respect, the process can be considered sustainable. Indeed, the process requires a minimum of synthetic steps, enabling access to complex molecules of undoubted therapeutic interest.

Supplementary Materials

1H and 13C NMR spectra of compounds 4a to 4h and 2D MDL molfile (in V2000 format) of the 9α-hydroxyparthenolide.

Author Contributions

Conceptualization, M.Z. and M.L.; methodology, M.Z. and M.L.; software, M.Z. and M.L.; validation, M.Z., M.L. and S.B.-R.; formal analysis, M.Z. and M.L.; investigation, M.Z. and M.L.; resources, M.Z. and M.L.; data curation, M.Z. and M.L.; writing—original draft preparation, M.Z. and M.L.; writing—review and editing, M.Z., M.L. and S.B.-R.; visualization, M.Z. and M.L.; supervision, M.Z. and M.L.; project administration, M.Z. and M.L. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Data Availability Statement

Data are contained within the article.

Conflicts of Interest

The authors declare no conflicts of interest.

Abbreviations

The following abbreviations are used in this manuscript:
PTLParthenolide
SLJSesquiterpene Lactone
NMRNuclear Magnetic Resonance

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Figure 1. Examples of biologically active sesquiterpene lactones.
Figure 1. Examples of biologically active sesquiterpene lactones.
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Figure 2. 9α-Hydroxyparthenolide extracted from Anvillea radiata.
Figure 2. 9α-Hydroxyparthenolide extracted from Anvillea radiata.
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Figure 3. 9α-Hydroxyparthenolide numbering system.
Figure 3. 9α-Hydroxyparthenolide numbering system.
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Scheme 1. Synthesis of spiro-isoxazolidine derivatives of 9α-hydroxyparthenolide.
Scheme 1. Synthesis of spiro-isoxazolidine derivatives of 9α-hydroxyparthenolide.
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Table 1. Optimization of operating conditions of the 1,3-dipolar cycloaddition reaction.
Table 1. Optimization of operating conditions of the 1,3-dipolar cycloaddition reaction.
EntrySolventTime (h)Nitrone (equiv.)Yield (a) (%)
1Toluene61.110
2Toluene121.120
3Toluene12224
4Benzene61.140
5Benzene121.176
6Benzene241.170
7Benzene121.576
(a) Yield of isolated product after column chromatography.
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MDPI and ACS Style

Zaki, M.; Loubidi, M.; Berteina-Raboin, S. Synthesis of Novel Spiro-Isoxazolidine Derivatives of 9α-Hydroxyparthenolide. Molbank 2025, 2025, M2054. https://doi.org/10.3390/M2054

AMA Style

Zaki M, Loubidi M, Berteina-Raboin S. Synthesis of Novel Spiro-Isoxazolidine Derivatives of 9α-Hydroxyparthenolide. Molbank. 2025; 2025(3):M2054. https://doi.org/10.3390/M2054

Chicago/Turabian Style

Zaki, Mohamed, Mohammed Loubidi, and Sabine Berteina-Raboin. 2025. "Synthesis of Novel Spiro-Isoxazolidine Derivatives of 9α-Hydroxyparthenolide" Molbank 2025, no. 3: M2054. https://doi.org/10.3390/M2054

APA Style

Zaki, M., Loubidi, M., & Berteina-Raboin, S. (2025). Synthesis of Novel Spiro-Isoxazolidine Derivatives of 9α-Hydroxyparthenolide. Molbank, 2025(3), M2054. https://doi.org/10.3390/M2054

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