Rapid access to the core of malayamycin A by intramolecular dipolar cycloaddition

• Yilin Liu,
• Yuchen Yang,
• Chen Yang,
• Sha-Hua Huang,
• Jian Jin and
• Ran Hong

Beilstein J. Org. Chem. 2025, 21, 2542–2547, doi:10.3762/bjoc.21.196

• details). The following reductive cleavage of the N–O bond was carried out by Mo(CO)6 in refluxing CH3CN [39]. Subsequent oxidation of the resulting secondary alcohol with Dess–Martin periodinane (DMP) [40] afforded methyl ketone 20 in 53% yield for 2 steps. Moreover, the minor isomer 19b also underwent

Transformation of the cyclohexane ring to the cyclopentane fragment of biologically active compounds

• Natalya Akhmetdinova,
• Ilgiz Biktagirov and
• Liliya Kh. Faizullina

Beilstein J. Org. Chem. 2025, 21, 2416–2446, doi:10.3762/bjoc.21.185

• (BnOH, 2,4,6-collidine, 160 °C). The desired benzyl ester 126 was isolated as single diastereomer with a yield of 56% yield. Reduction of 126 with LiAlH4 followed by oxidation with Dess–Martin periodinane (DMP) led to the synthesis of a key aldehyde 127, with a yield of 75% in two steps. The target

• trimethylamine N-oxide and Dess–Martin periodinane, α-selenylation, and hydrogen peroxide-induced selenoxide elimination led to unsaturated ketone 183, from which artalbic acid (180) was obtained through a series of chemical transformations. The synthetic versatility of the photoinduced carboborative ring

Recent advances in Norrish–Yang cyclization and dicarbonyl photoredox reactions for natural product synthesis

• Peng-Xi Luo,
• Jin-Xuan Yang,
• Shao-Min Fu and
• Bo Liu

Beilstein J. Org. Chem. 2025, 21, 2315–2333, doi:10.3762/bjoc.21.177

• delivered 68. A one-pot desilylation/oxidation of 67 produced an aldehyde, which was subject to selective nucleophilic addition in the presence of a ketone, allowing for access to the furan precursor 68 [37]. Oxidation–cyclization–aromatization of 68 with Dess–Martin periodinane (DMP) constructed the

Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis

• Lihua Wei,
• Rui Yang,
• Zhifeng Shi and
• Zhiqiang Ma

Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151

• transformation of 145, compound 146 was oxidized with Dess-Martin periodinane (DMP). Subsequent reductive amination with fragment 139 provided an intermediate, which underwent the second reductive amination using formaldehyde. This one-pot process with concomitant deprotection afforded acid 147 in 70% yield over

Synthetic approach to borrelidin fragments: focus on key intermediates

• Yudhi Dwi Kurniawan,
• Zetryana Puteri Tachrim,
• Teni Ernawati,
• Faris Hermawan,
• Ima Nurasiyah and
• Muhammad Alfin Sulmantara

Beilstein J. Org. Chem. 2025, 21, 1135–1160, doi:10.3762/bjoc.21.91

• with LiAlH4, followed by oxidation of the resulting primary alcohol with Dess–Martin periodinane, gave the anticipated aldehyde 147 in 76% yield over two steps. In the final stage, compound 137 was converted to organomagnesium intermediate 148 upon treatment with isopropylmagnesium bromide in THF and

Hydrogen-bond activation enables aziridination of unactivated olefins with simple iminoiodinanes

• Phong Thai,
• Lauv Patel,
• Diyasha Manna and
• David C. Powers

Beilstein J. Org. Chem. 2024, 20, 2305–2312, doi:10.3762/bjoc.20.197

• ), Koser’s reagent (PhI(OH)OTs), Zhdankin’s reagent (C6H4(o-COO)IN3, ABX), and Dess–Martin periodinane (DMP) – and find application in an array of synthetically important transformations including olefin difunctionalization, carbonyl desaturation, alcohol oxidation, and C–H functionalization [3][4

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

• Haifeng Yu,
• Wanting Zhang,
• Xuejing Cui,
• Zida Liu,
• Xifu Zhang and
• Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

• ) [25] or β-keto esters (Scheme 1a, path 4) [26][27], the aldol reaction between aldehydes and S-ethyl acetothioate followed by oxidation with Dess–Martin periodinane (Scheme 1a, path 5) [28], the hydrolysis of α-oxo ketene dithioacetals (Scheme 1a, path 6) [29] and MgBr2·OEt2-catalyzed acylation of

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ³-iodanes

• Thomas J. Kuczmera,
• Pim Puylaert and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

• established in several oxidative transformations including the synthesis of complex molecules and drugs [12][13]. The most prominent examples are the pentavalent derivatives 2-iodoxybenzoic acid (IBX) and Dess–Martin periodinane (DMP) [14][15]. Although mild and selective oxidants, these highly oxidized λ5

(Bio)isosteres of ortho- and meta-substituted benzenes

• H. Erik Diepers and
• Johannes C. L. Walker

Beilstein J. Org. Chem. 2024, 20, 859–890, doi:10.3762/bjoc.20.78

• oxidation of alcohol 175 with Dess–Martin periodinane. Synthesis of cubane 166 was then achieved by [2 + 2] cycloaddition of enone 176 using acetone as the photosensitiser (to 177), the first Favorskii ring contraction (to 178), deketalisation, the second Favorskii ring contraction and esterification (to

Asymmetric synthesis of a stereopentade fragment toward latrunculins

• Benjamin Joyeux,
• Antoine Gamet,
• Nicolas Casaretto and
• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 428–433, doi:10.3762/bjoc.19.32

• reduced on its primary carbon in presence of LiAlH4, and the resulting secondary alcohol was oxidized in presence of Dess–Martin periodinane (DMP), giving ketone 15 in 78% yield over the two steps. This six-step sequence to 15 was performed in a 35% overall yield from starting material 10. The aldehyde

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

• János Máté Orosz,
• Dóra Ujj,
• Petr Kasal,
• Gábor Benkovics and
• Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

• corresponding carboxylic acid derivatives [20]. An alternative strategy to overcome the difficulties associated with the preparation of mono-6-O-tosyl-CD intermediates is the direct preparation of 6-monoaldehyde-CD with Dess–Martin periodinane in a fairly good yield of 85%, which can be considered the most

Total synthesis of grayanane natural products

• Nicolas Fay,
• Rémi Blieck,
• Cyrille Kouklovsky and
• Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

• -disubstituted olefin and reductive epoxide ring-opening giving triol 18. After oxidation of the primary and the secondary alcohols with Dess–Martin periodinane, the remaining tertiary alcohol was protected as a MOM ether and the silyl ether protecting group was removed. The obtained intermediate 19 was then a

• corresponding ketone was achieved using Dess–Martin periodinane with a pyridine buffer. Addition of Me3SiCH2Li efficiently afforded the Peterson adduct 33. The 1,1-disubtituted alkene was then submitted to Mukaiyma hydration to form the tertiary alcohol, in presence of Mn(dpm)3, PhSiH3 and O2. Then, the ketone

Vicinal ketoesters – key intermediates in the total synthesis of natural products

• Marc Paul Beller and
• Ulrich Koert

Beilstein J. Org. Chem. 2022, 18, 1236–1248, doi:10.3762/bjoc.18.129

• with Davis’ oxaziridine and subsequent oxidation using Dess–Martin periodinane. Initial attempts for the key step (15 → 16) like a Nozaki–Hiyama–Kishi reaction failed, but lithium–halogen exchange using t-BuLi at low temperatures gave the desired vinyllithium intermediate I which successfully added to

Synthesis of highly substituted fluorenones via metal-free TBHP-promoted oxidative cyclization of 2-(aminomethyl)biphenyls. Application to the total synthesis of nobilone

• Ilya A. P. Jourjine,
• Lukas Zeisel,
• Jürgen Krauß and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2668–2679, doi:10.3762/bjoc.17.181

• nitrate (CAN) [41], 2,2,6,6-tetramethylpiperidinyloxyl (TEMPO)/CuCl [51], K2S2O8 [36], dimethyl sulfoxide (DMSO)/O2 [52], PhI(OAc)2/benzoyl peroxide (BPO) [47], Dess-Martin periodinane, N-bromosuccinimide (NBS), N-hydroxyphthalimide (NHPI)/Co(OAc)2/O2 [53], H2O2/tetrabutylammonium iodide (TBAI) [43], CBr4

Recent advances in the syntheses of anthracene derivatives

• Giovanni S. Baviera and
• Paulo M. Donate

Beilstein J. Org. Chem. 2021, 17, 2028–2050, doi:10.3762/bjoc.17.131

• DIBAL-H reduction, and later to aldehydes 199 by Dess–Martin periodinane (DMP) oxidation. The aldehydes 199 were treated with BINOL-PO2H in chloroform, in the presence of air and light, to produce the corresponding anthraquinones 200 in excellent yields (93–99%) [82]. In this review, a more detailed

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols

• Jie Zheng,
• Shuyu Meng and
• Quanrui Wang

Beilstein J. Org. Chem. 2021, 17, 1481–1489, doi:10.3762/bjoc.17.104

• alcohol using Dess–Martin periodinane [19][20]. The reported methods involved the use of ethylene oxide, a hazardous and carcinogenic gas. This prompted us to work out a more practical and flexible method to access the aromatic enal compounds 13. At the offset, we examined the synthesis of 2-(2

α,γ-Dioxygenated amides via tandem Brook rearrangement/radical oxygenation reactions and their application to syntheses of γ-lactams

• Mikhail K. Klychnikov,
• Radek Pohl,
• Ivana Císařová and
• Ullrich Jahn

Beilstein J. Org. Chem. 2021, 17, 688–704, doi:10.3762/bjoc.17.58

• (general procedure) A solution of hydroxy lactam 12 or trans-12 (0.7 mmol) in dichloromethane (4 mL) was added to a stirred solution of Dess–Martin periodinane (386 mg, 0.9 mmol) and t-BuOH (0.1 mL, 1.1 mmol) in dichloromethane (4 mL) at room temperature. After 30 min, saturated Na2CO3 solution (2 mL) and

Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

• Takashi Yamazaki,
• Yoh Nakajima,
• Minato Iida and
• Tomoko Kawasaki-Takasuka

Beilstein J. Org. Chem. 2021, 17, 132–138, doi:10.3762/bjoc.17.14

• substituent in this position, a full conversion was not observed even after a prolonged reaction period and at a higher temperature, and such conditions seemed to evoke the degradation of the products 2 to some extent. This was not the case for the Dess–Martin periodinane oxidation and the propargylic

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

• Dimas J. P. Lima,
• Antonio E. G. Santana,
• Michael A. Birkett and
• Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

• corresponding ammonium salt (±)-106 in 73% yield. The N–O bridge of ammonium salt (±)-106 was reduced with zinc. The resulting diastereomerically pure amino alcohol (±)-107 was then oxidized in the presence of Dess–Martin periodinane to deliver N-methyleuphococcinine ((±)-3). Although Kurtis' synthesis was

• -carboxaldehyde, 9:1 77a/77b, 67% (after chromatographic separation); ii) butyl vinyl ether, Hg(OAc)2, (10 mol %), sealed tube, 130–135 °C, 79%; iii) vinylmagnesium bromide, −78 °C; iv) Dess–Martin periodinane, 83% over two steps; v) Grubbs catalyst 2nd gen., CH2Cl2, reflux, 74%; vi) 1. (PhSe)2, NaBH4, EtOH; 2

• ; 2. 1-heptyne; 3. I2, THF, 82%; ii) 1. n-BuLi, Et2O, −78 °C to 0 °C; 2. p-menthyl-3-carboxaldehyde, 5:1 (−)-87a / (−)-87b, 50% (after chromatographic separation); iii) butyl vinyl ether, Hg(OAc)2, (10 mol %), sealed tube, 130–135 °C, 79%; iv) vinylmagnesium bromide, −78 °C; v) Dess–Martin periodinane

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration–oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles

• Lívia Dikošová,
• Júlia Laceková,
• Ondrej Záborský and
• Róbert Fischer

Beilstein J. Org. Chem. 2020, 16, 1313–1319, doi:10.3762/bjoc.16.112

• isoxazolidin-4-ols. The strategy relies on a highly regio- and trans-stereoselective hydroboration–oxidation reaction of the 4,5-unsubstituted 2,3-dihydroisoxazoles with basic hydrogen peroxide. The consecutive oxidation/reduction route, sequentially employing Dess–Martin periodinane and ʟ-selectride, is used

• (Scheme 3). Dess–Martin periodinane was chosen as the oxidizing agent [33][34] as our primary choice, pyridinium dichromate, prove to be insufficiently effective even at an elevated temperature. The reaction in anhydrous dichloromethane at 0 °C led to the desired isoxazolidin-4-ones 9a–c in moderate

• isoxazolidin-4-ols with Dess–Martin periodinane (±)-2-Benzyl-3-phenylisoxazolidin-4-one (9a): A Schlenk flask was charged with the isoxazolidinol 8a (450 mg, 1.76 mmol), evacuated, and filled with argon. The starting material was dissolved in anhydrous CH2Cl2 (18 mL), the reaction mixture was cooled down to 0

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• with LiBH4 resulted in alcohol 124 which was oxidized by Dess–Martin periodinane to give (S)-(−)-2-fluoro-2-phenylacetaldehyde (125). This aldehyde is prone to racemization and decomposition and therefore was directly converted to the arylidene derivative 127, by treatment with p-toluenesulfinamide

Copper-promoted/copper-catalyzed trifluoromethylselenolation reactions

• Clément Ghiazza and
• Anis Tlili

Beilstein J. Org. Chem. 2020, 16, 305–316, doi:10.3762/bjoc.16.30

• form C(sp)–SeCF3 bonds (Scheme 3) [18]. Therein, Dess–Martin periodinane (DMP) was used as the oxidant and potassium fluoride as the base, and the reactions were performed at room temperature in DMF as the solvent. The desired compounds were obtained in moderate to very good yields. Both electron

A toolbox of molecular photoswitches to modulate the CXCR3 chemokine receptor with light

• Xavier Gómez-Santacana,
• Sabrina M. de Munnik,
• Tamara A. M. Mocking,
• Niels J. Hauwert,
• Shanliang Sun,
• Prashanna Vijayachandran,
• Iwan J. P. de Esch,
• Henry F. Vischer,
• Maikel Wijtmans and
• Rob Leurs

Beilstein J. Org. Chem. 2019, 15, 2509–2523, doi:10.3762/bjoc.15.244

• was selectively reduced with DIBAL-H to benzyl alcohols 23f–h, which were oxidized with Dess–Martin periodinane to the corresponding benzaldehyde 26f–h. Reductive amination of 26f–h with 7 gave the tertiary amines 13f–h. Methylation with iodomethane and subsequent precipitation gave 3f–h as orange

• oxidation of methyl 5-amino-2-chlorobenzoate (17c) with Oxone® to 18c, which was used in a Mills reaction with 2-iodoaniline (19a) to yield azobenzene 21. The methyl ester was selectively reduced with DIBAL-H and the resulting alcohol 24 oxidized with Dess–Martin periodinane to benzaldehyde 27. Reductive

• , 61–96%; (c) i) DIBAL-H (3.0–4.0 equiv), THF, 0–5 °C to rt, 2–4 h; ii) NH4Cl (aq), Rochelle salt (10% aq), EtOAc, 1–2 h, 76–99%; or for 23h i) DIBAL-H (1.2 equiv) , DCM, −78 °C, 1 h; ii) MeOH, −78 °C to rt, 0.5 h, iii) Rochelle salt (10% aq), 3 h, 45%; (d) Dess–Martin periodinane (1.0 equiv), DCM, rt

Thermal stability of N-heterocycle-stabilized iodanes – a systematic investigation

• Andreas Boelke,
• Yulia A. Vlasenko,
• Mekhman S. Yusubov,
• Boris J. Nachtsheim and
• Pavel S. Postnikov

Beilstein J. Org. Chem. 2019, 15, 2311–2318, doi:10.3762/bjoc.15.223

• explosive properties of Togni’s reagent and very recently, Williams and co-workers analyzed the sensitivity of common oxidants including 2-iodoxybenzoic acid (IBX) and Dess–Martin periodinane (DMP) [19][20]. Waser and co-workers examined the thermal stability of the Zhdankin reagent ABX and compared it with