Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Solid-phase total synthesis and structural confirmation of antimicrobial longicatenamide A

• Takumi Matsumoto,
• Takefumi Kuranaga,
• Yuto Taniguchi,
• Weicheng Wang and
• Hideaki Kakeya

Beilstein J. Org. Chem. 2022, 18, 1560–1566, doi:10.3762/bjoc.18.166

• )-protected ᴅ-serine 12 (Scheme 2). Treatment of the olefin 15 with trifluoroacetic acid (TFA) cleaved the Boc protecting group and the acetonide to deliver unsaturated amino alcohol 16. The amino group in 16 was protected by the fluorenylmethyloxycarbonyl (Fmoc) protecting group for solid-phase peptide

Efficient synthesis of aziridinecyclooctanediol and 3-aminocyclooctanetriol

• Emine Salamci and
• Ayse Kilic Lafzi

Beilstein J. Org. Chem. 2022, 18, 1539–1543, doi:10.3762/bjoc.18.163

• ]. Furthermore, aziridine derivatives are valuable precursors for the synthesis of aminocyclitols, which can be found in nature in several families of natural and clinically important antibiotics [10]. Aminocyclitols containing the amino alcohol motif are important structural components for modifying bioactive

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

• Sumana Mandal,
• Raju D. Chaudhari and
• Goutam Biswas

Beilstein J. Org. Chem. 2021, 17, 2348–2376, doi:10.3762/bjoc.17.153

• -amino alcohol 38 leading to the formation of (1R,2R,6R)-9-benzyl-9-azabicyclo[4.2.1]nonan-2-ol (39). The bicyclic derivative 39 through the number of consequent reactions formed a highly potent (+)/(−)-pyrido[3,4-b]homotropane (40), a bridged nicotinoid (Scheme 15) [61]. Similarly, precursor 41 at room

• cyclization of alkenyl α-aminophosphonates. Cyclization of 4-cycloocten-1-ol with Hg(OAc)2 forming fused bicyclic products. trans-Amino alcohol formation through Hg(II)-salt-mediated cyclization. Hg(OAc)2-mediated 2-aza- or 2-oxa-bicyclic ring formations. Hg(II)-salt-induced cyclic peroxide formation. Hg(OAc

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

• LiH2NBH3 in THF at 40 °C to provide amino alcohol (−)-44 in 88% yield. This amino alcohol underwent cyclization through a one-pot process in the presence of TPAP-NMO, which involved oxidation in generated aldehyde 45, followed by dehydrocondensation leading to N,O-tricyclic acetal (−)-46 in 80% yield

• 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

Recent developments in enantioselective photocatalysis

• Callum Prentice,
• James Morrisson,
• Andrew D. Smith and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

• •−, which adds to the nitrone via a proposed 6-membered transition state to afford radical cation 286•+. Subsequent hydrogen atom abstraction from TEEDA•+ generates complex 286−. Protonation and displacement by other substrate molecules releases the desired 1,2-amino alcohol products 287 in excellent yields

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• oxazolidinones and five-membered cyclic carbonates of various structures. The most well-known strategies for the synthesis of oxazolidinones are the reaction of an amino alcohol with phosgene [5][22], the carbonylation reaction of β-amino alcohols with CO2 or dialkyl carbonates [23][24][25][26][27], the

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

• the primary hydroxy group (Alloc) gave alcohol 117 in good yield. The fluorination of 117 was achieved by treatment with DAST to form 118. Then, selective removal of the Alloc protecting group using Pd(PPh3)4, was followed by oxidation of the resulting Boc-protected amino alcohol 119 to give the N-Boc

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

• Marcin Kaźmierczak and
• Henryk Koroniak

Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69

• equiv) or PBSF (1,2 equiv) and base (2 equiv) were added under an argon atmosphere to a stirred solution of amino alcohol 5 (1mmol) in 2,5 mL PhMe, under an argon atmosphere. The reaction mixture was stirred at room temperature until completion of the reaction monitored by TLC (3–18 h). The reaction

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• -oxazaphosphorine ligands with a P-center and backbone chirality (Scheme 24). Spiro-1,3-amino alcohol compounds 124 were synthesized according to a literature procedure [107]. For the synthesis of the mono-N-methylated amino alcohol ligands a cooled solution of dichlorophenylphosphine was treated with triethylamine

• protocol with free amine spiro-amino alcohol derivative 124 gave compounds 125 and 127 (R = H) in low yields. An optimized procedure was used where dichlorophenylphosphine and borane·dimethyl sulfide in tetrahydrofuran were premixed at −78 °C. The temperature was then raised to 25 °C before neutralizing

• with triethylamine. Finally, spiro-1,3-amino alcohol was added and an equimolar mixture of compounds 125 and 127 was obtained with good yields. The dimeric ligands 126 and 128 were obtained by coupling each mono ligand in THF by first treating with potassium butoxide with subsequent addition of

N-(1-Phenylethyl)aziridine-2-carboxylate esters in the synthesis of biologically relevant compounds

• Iwona E. Głowacka,
• Aleksandra Trocha,
• Andrzej E. Wróblewski and
• Dorota G. Piotrowska

Beilstein J. Org. Chem. 2019, 15, 1722–1757, doi:10.3762/bjoc.15.168

• diversified compounds. In this review we wish to focus attention on applications of 5–8 in syntheses of biologically important compounds having a 2-amino-1,3-disubstituted propane unit implanted into their structures because vicinal amino alcohol and 2-aminopropane-1,3-diol scaffolds are present in many

• NaBH4/ZnCl2 mixture (chelation controlled) gave the aziridine alcohol 20 as a major product. Reductive opening of the aziridine ring produced the amino alcohol 21 which was transformed into the substituted oxazolidin-2-one 22. Its catalytic hydrogenation effected deoxygenation at the benzylic position

• followed by protection of the amino alcohol and Birch debenzylation to give 137. After basic hydrolysis and N-protection to form 138 a two-step hydroxymethyl to carboxyl oxidation was performed to yield N-Boc-norfuranomycin ((2S,2'R)-133). Installation of the 1-methylprop-2-en-1-yl group in (2R,1'R,1''R

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• hydrolyzed in the acidic phagolysosome [39][41][46]. To improve the overall synthetic sequence from our previous syntheses [11][41][42], an amino alcohol spacer was utilized to connect the trimannose reducing end to the dendrimer by means of amide bond coupling. Furthermore, the amino alcohol spacer provides

• (emission maximum 580 nm). The latex-bead synthesis was modified slightly from previous synthesis for improved ease of synthesis of trimannose and comparability to this study’s bioerodible microparticles by coupling the reducing end of trimannose with the aforementioned amino alcohol spacer [11][41

• trichloroacetimidate mannosyl donors 3 and 4 [47][50] and the use of a fluorous tag containing an amino alcohol spacer rather than an alkene that would require late-stage modifications. The aminopentanol spacer 6 used at the reducing end to conjugate to the dendrimer was first protected with fluorous CbzF-NHS 5 to

A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12

• Seema V. Kanojia,
• Sucheta Chatterjee,
• Subrata Chattopadhyay and
• Dibakar Goswami

Beilstein J. Org. Chem. 2019, 15, 490–496, doi:10.3762/bjoc.15.42

• (1R,3S)-HPA-12 (2) used the chiral pool approach [15][16], crystallization-induced asymmetric transformation [17], diastereoselective reduction of γ-aryl-γ-oxo-β-amino alcohol [18], cycloaddition of oxime with alkenes [19], enantioselective carbonyl reduction followed by an organocatalyzed α-amination

Stereoselective total synthesis and structural revision of the diacetylenic diol natural products strongylodiols H and I

• Pamarthi Gangadhar,
• Sayini Ramakrishna,
• Ponneri Venkateswarlu and
• Pabbaraja Srihari

Beilstein J. Org. Chem. 2018, 14, 2313–2320, doi:10.3762/bjoc.14.206

• to long chain aliphatic aldehydes in the presence of N-methylephedrine [17] or an amino alcohol–zinc complex [18] and the Cadiot–Chodkiewicz cross-coupling reaction as key steps [14][15][16]. In continuation to our research interest on the synthesis of acetylenic compounds [19][20][21], recently we

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• asymmetric Michael addition reaction of thiophenol could be catalyzed by inherently chiral calixarenes bearing amino alcohol/phenol structure [47][48]. In order to see the effect of the diarylmethanol moiety, Shirakawa and Shimizu used 43 (Figure 6) as organocatalyst in the Michael addition reaction between

• 2-cyclohexen-1-one (44) and thiophenol (45, Scheme 12) [37]. Compared to the inherently chiral calix[4]arene bearing an amino alcohol structure, a beneficial effect of the additional diaryl group was confirmed and the product was obtained in 23% ee with 81% yield. Substituted thiophenols, 2

Fluorocyclisation via I(I)/I(III) catalysis: a concise route to fluorinated oxazolines

• Felix Scheidt,
• Christian Thiehoff,
• Gülay Yilmaz,
• Stephanie Meyer,
• Constantin G. Daniliuc,
• Gerald Kehr and
• Ryan Gilmour

Beilstein J. Org. Chem. 2018, 14, 1021–1027, doi:10.3762/bjoc.14.88

• diastereoselective on account of the proximal nature of the stereocentre (65%, dr >95:5). Compound 3 is noteworthy on account of the β-amino alcohol and β-fluoro alcohol motifs that collectively preorganised the propyl chain. Stabilising hyperconjugative interactions manifest themselves in the characteristic gauche

Recent developments in the asymmetric Reformatsky-type reaction

• Hélène Pellissier

Beilstein J. Org. Chem. 2018, 14, 325–344, doi:10.3762/bjoc.14.21

• alcohols and BINOL (1,1’-bi-2-naphthol) derivatives, ligand 53 was selected as optimal ligand when used at a stoichiometric amount in THF at −40 °C. As shown in Scheme 21, the corresponding fluorinated chiral β-amino alcohol 54 was formed in both moderate yield (60%) and enantioselectivity (37% ee

• of related molecules. Aza-Reformatsky reactions Especially, several excellent results have been recently reported in the area of enantioselective catalytic aza-Reformatsky reactions by using chiral 1,2-amino alcohols and diarylprolinols as ligands. For example, chiral 1,2-amino alcohol (1R,2S)-59 was

• reagents in enantioselective reactions with imines catalyzed by catalytic amounts of chiral 1,2-amino alcohol ligands in the presence of ZnEt2 as the zinc source. Moreover, the first use of cyclic imines, including low reactive cyclic ketimines, in enantioselective aza-Reformatsky reactions with ethyl

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• these valuable synthetic intermediates. We envisioned a process wherein a 1,2-amino alcohol 1 would undergo condensation with an appropriate quinone catalyst 2 to deliver iminoquinone 3 (Scheme 2). Deformylation of 3 would generate N-arylimine 4. Subsequent transimination with amine 6 would provide the

• scope of this methodology by employing a range of 1,2-amino alcohol substrates 1 (Table 2). As reported in Table 1, the reaction involving phenylglycinol gave the desired N-PMP imine (7a) in 85% yield (Table 2, entry 1). ortho-Substitution of the arene is reasonably well-tolerated, as 2

•  2, entries 5−9). Both electron-donating and electron-withdrawing substituents were tolerated, but no obvious trends in the reactivity patterns were observed (47−77% yield). Thiophenyl amino alcohol 1j was also subjected to the optimized conditions and the corresponding imine 7j was formed in 47

Acid-catalyzed ring-opening reactions of a cyclopropanated 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols

• Katrina Tait,
• Alysia Horvath,
• Nicolas Blanchard and
• William Tam

Beilstein J. Org. Chem. 2017, 13, 2888–2894, doi:10.3762/bjoc.13.281

• ] and 1D NOESY 1H NMR the stereochemistry of the products was confirmed, with the nucleophile added syn to the cyclopropane ring and anti to the amino alcohol group. When forming the ring-opening product, there are two possible mechanisms (Scheme 6). If the oxygen atom is first protonated followed by

Continuous N-alkylation reactions of amino alcohols using γ-Al₂O₃ and supercritical CO₂: unexpected formation of cyclic ureas and urethanes by reaction with CO₂

• Emilia S. Streng,
• Darren S. Lee,
• Michael W. George and
• Martyn Poliakoff

Beilstein J. Org. Chem. 2017, 13, 329–337, doi:10.3762/bjoc.13.36

• the presence of scCO2 and thus proceeds faster than the intermolecular reaction. We also explored the cyclisation and N-alkylation of different amino alcohol substrates. Initially we investigated the effect of simply changing the alkane chain length. Starting with 4-amino-1-butanol (3) under the model

• temperature of the reactor, the residence time and to some extent the concentration of the amino alcohol in the alcohol. A higher pressure of CO2 appears to slow the rate of conversion of 13 to 14, whilst elevated temperatures appear to accelerate the rate. Increasing the residence time allows more time for

• higher temperatures in both the presence and absence of scCO2. Increasing the primary alcohol length led to slightly lower yields of the target products whereas secondary alcohols did not react with the amines at all. Varying the chain length of the amino alcohol produced the corresponding N-alkylated

Solution-phase automated synthesis of an α-amino aldehyde as a versatile intermediate

• Hisashi Masui,
• Sae Yosugi,
• Shinichiro Fuse and
• Takashi Takahashi

Beilstein J. Org. Chem. 2017, 13, 106–110, doi:10.3762/bjoc.13.13

• aldehyde (4a) and its analogues are very important versatile intermediates. The automated synthesis of 4a can be applied to the synthesis of various useful compounds containing a vicinal amino alcohol moiety. Full picture of ChemKonzert, showing two reaction vessels (RF1 and RF2), a centrifugal separator

Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

• Michal Medvecký,
• Igor Linder,
• Luise Schefzig,
• Hans-Ulrich Reissig and
• Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

• . This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor. Keywords: amino alcohol; click reaction; cross-coupling reactions; hydrogenation; iodination; 1,2-oxazines; Introduction Over the last decade, we have intensively

• alcohol derivative 27 in 51% yield as 96:4 mixture of two diastereomers (Scheme 9). Subsequent ring closure of γ-amino alcohol 27 by treatment with mesyl chloride in the presence of triethylamine [53] furnished the N-mesylated pyrrolidine derivative 28 in 65% yield with excellent diastereoselectivity (dr

• therefore briefly examined the reaction of 5-aryl-substituted 1,2-oxazines syn-21 and anti-24 under previously established conditions [53]. The hydrogenolysis of 1,2-oxazine derivative syn-21 in methanol using palladium on charcoal as catalyst afforded the expected α-(3-methoxyphenyl)-substituted γ-amino

A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis

• Mariano Goldberg,
• Denis Sartakov,
• Jan W. Bats,
• Michael Bolte and
• Michael W. Göbel

Beilstein J. Org. Chem. 2016, 12, 1870–1876, doi:10.3762/bjoc.12.176

• , batches larger than 15 g of the S-configurated acid 13 could be isolated in 90% yield (45% based on rac-12). In a two-step procedure 13 was converted into amino alcohol 14 without recrystallization in order to keep the enantiomeric excess unchanged. It was determined at this stage to be better than 99

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

• Bin Yu,
• Hui Xing,
• De-Quan Yu and
• Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

• . Substituents attached to the isatins and ketones had little effect on the yields and enantioselectivity, regardless of their electronic properties and positions. Amino alcohol catalysts In 2014, Evano and co-workers reported a concise synthesis of the macrocyclic core of TMC-95A using the asymmetrc aldol

• the aldolization step can be carried out on a multigram scale. Very recently, Tsogoeva and co-workers reported the amino alcohol-catalyzed one-pot enantioselective synthesis of antileukaemia agent (R)-convolutamydine A in 95% yield and with 85% ee under mild conditions (Scheme 23) [39]. Notably, the

• amino alcohol catalysts were generated in situ from the corresponding amino acids L-Leu or L-Val through the BH3-mediated reduction, making the multi-step synthesis more efficient and environmentally friendly. Diamine catalysts In 2013, Chimni and co-workers reported the diamine catalyst (cat. 10

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• . synthesised the hydroxyleucine moiety found in naturally occurring muraymycins of classes A to C (Scheme 8) [107]. Adapting a strategy developed by Zhu et al., D-serine (59) was stereoselectively converted into the protected amino alcohol 60 [108]. Key intermediate 60 was then Cbz- and acetonide protected to