- Structural elucidation, total synthesis, and cytotoxic activity of effphenol A
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A highly substituted phenol derivative, effphenol A (1), was isolated from the deep-sea-derived fungus Trichobotrys effuse FS524. Its complete structural assignment was established through a combination of spectroscopic analysis together with single-crystal X-ray diffraction experiments and further unequivocally confirmed by a biomimetic total synthesis. Structurally, effphenol A possesses a poly-substituted 6-5/6/6 tetracyclic ring system, which represents the first case of such a skeleton found in nature. Furthermore, the cytotoxic activity of effphenol A (1) toward four human cancer cell lines was assayed. This journal is
- Chen, Shanchong,Chen, Yuchan,Dong, Chunmao,Liu, Hongxin,Liu, Zhaoming,Tan, Haibo,Zhang, Weimin,Zhang, Xiao
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Read Online
- Selective methylation of phloroglucinol in the presence of a glycoluril clip
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Methylation of phloroglucinol was performed using dimethyl sulfate as the methylating agent in the presence and absence of a glycoluril clip. The results showed that the yield of the di-methylated product decreased significantly in the presence of a glycoluril clip (host), due to the formation of a host-guest complex between the clip and phloroglucinol. Also, the reaction was conducted with different quantities (mol %) of the host.
- Rezaei-Seresht, Esmail,Maleki, Behrooz,Amiri-Moghaddam, Zeinab,Taghizadeh, Sara
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Read Online
- Selective Catalytic Methylation of Phloroglucinol with Dimethyl Carbonate in the Presence of Heterogeneous Acids
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A facile process for the methylation of phloroglucinol using environmentally friendly dimethyl carbonate as methylating agent and solvent is described. Widely available and inexpensive solid acids have been used as catalysts to promote this transformation. H-Y zeolite proved particularly selective for monomethylation, hence it has been used for the convenient preparation of methoxyresorcinol (MR), with only limited co-production of dimethoxyphenol (DMP). Conversely, the use of tungstosilicic acid on silica easily afforded DMP in excellent isolated yield.
- Lui, Matthew Y.,Noè, Marco,Masters, Anthony F.,Maschmeyer, Thomas
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Read Online
- An efficient synthesis of bergapten
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An efficient synthesis of the linear furanocoumarin, bergapten, is reported. In order to avoid the formation of the angular furanocoumarin, we have adopted iodine as protecting group at the 8 position of the coumarin ring.
- Oda, Kazuaki,Nishizono, Naozumi,Tamai, Yukio,Yamaguchi, Yuki,Yoshimura, Teruki,Wada, Keiji,Machida, Minoru
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Read Online
- Total syntheses of hyperaspidinols A and B enabled by a bioinspired diastereoselective cascade sequence
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A bioinspired acid-triggered hemiacetalization/dehydration/[3 + 3]-type cycloaddition cascade process was disclosed, diastereoselectively furnishing furo[2,3-b]chromene skeleton under mild conditions. The viability of this approach was demonstrated by syntheses of a series of furo[2,3-b]chromene and pyrano[2,3-b]chromene derivatives. The successful total syntheses of two lignan-phloroglucinol hybrids, hyperaspidinols A and B, exemplified the synthetic utility of our biomimetic methodology.
- Chen, Huiyu,Lu, Xiuxiang,Tan, Haibo,Wang, Sasa,Zhang, Wenge,Zheng, Anquan,Zhou, Tingting
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supporting information
(2021/09/03)
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- Total syntheses of (+)-adunctins C and D: Assignment of their absolute configurations
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The first total synthesis of (+)-adunctin C (ent-1) and (+)-adunctin D (2), two monoterpene-substitued dihydrochalcones isolated from Piper aduncum (Piperaceae), was achieved. A regioselective oxidative [3 + 2] cycloaddition of acylphloroglucinol with (-)-β-phellandrene was developed to construct their unique spirobenzofuran skeleton. The absolute configurations of natural adunctins 1 and 2 were thus assigned through these endeavors. This journal is
- Luo, Gan,Peng, Yu,Wang, Ya-Wen,Xiao, Jian,Zhao, Jun
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supporting information
p. 9840 - 9843
(2021/12/07)
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- Design, synthesis, and biological activity studies of a new class of sulfonated aurones: First synthesis of acidoaurone isolated from Phyllanthus acidus
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A novel series of aurones were designed by introducing sulfonic acid group on ring-A and ring-B of known natural aurones such as hispidol, sulfuretin, maritimetin, and aureusidin. These sulfonated aurones were synthesized by a unique approach. Sulfonation on ring-A or ring-B converts water-insoluble aurones into highly water-soluble aurones. The sulfonated aurones were tested for their antioxidant, antiinflammatory, and AChE inhibition activities along with their natural aurones. Ring-A sulfonated aurones displayed higher antioxidant activity, 5-LOX, and AChE inhibition in comparison with their corresponding natural aurones. Ring-B sulfonated aurones exhibited potent 5-LOX inhibitory activity and significant antioxidant activity. Acidoaurone, a first sulfonated aurone isolated from Phyllanthus acidus was synthesized for the first time and was well characterized using NMR, LC–MS, and further confirmed by HMBC.
- Venkateswarlu, Somepalli,Murty, Gandrotu Narasimha,Satyanarayana, Meka,Siddaiah, Vidavalur
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p. 2324 - 2333
(2021/09/25)
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- SYNTHESIS OF MORIN AND MORIN DERIVATIVES
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The invention relates to a method for directly producing morin derivatives and high-purity morin of formula (I). The invention also relates to morin derivatives and high-purity morin that can be obtained using the claimed method.
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Paragraph 0031; 0033
(2020/11/24)
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- Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo
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Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)-1 and (S)-1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC-ECD coupling. (R)-1 and (S)-1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)-enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short- and long-term memory at low dosages.
- Hofmann, Julian,Fayez, Shaimaa,Scheiner, Matthias,Hoffmann, Matthias,Oerter, Sabrina,Appelt-Menzel, Antje,Maher, Pamela,Maurice, Tangui,Bringmann, Gerhard,Decker, Michael
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supporting information
p. 7299 - 7308
(2020/05/18)
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- Preparation method of spirobenzofuran compounds
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The invention discloses a preparation method of spirobenzofuran compounds. The method comprises the steps: taking commercially available phloroglucinol and 4-isopropyl cyclohexanone as raw materials;dihydrochalcone and beta-phellandrene with an extracyclic double bond are respectively synthesized through a Friedel-Crafts reaction and a Wittig reaction; after two fragment compounds of the hydrochalcone and the beta-phellandrene are obtained, with oxidized cycloaddition reactions, connecting the two fragment compounds, constructing a spirobenzofuran core skeleton, and thus preparing natural products adunctin C and adunctin D. According to the invention, an organic chemical synthesis means is adopted, synthesis of the target natural products adunctin C and adunctin D is used as guidance, anda new method for constructing the structural units is developed; meanwhile, the method is applied to synthesis and preparation of the natural products adunctin C and D with important physiological and pharmacological activities, the preparation yield is high, the cost is low, and the limitation of sources of the natural products is greatly broken through.
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Paragraph 0009; 0027
(2020/11/12)
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- Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base
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The combined use of an organic base for resorcinols realized a Kolbe-Schmitt type reaction under ambient conditions. When resorcinols (3-hydroxyphenol derivatives) were treated with DBU under a carbon dioxide atmosphere, nucleophilic addition to carbon dioxide proceeded to afford the corresponding salicylic acid derivatives in high yields.
- Sadamitsu, Yuta,Okumura, Akira,Saito, Kodai,Yamada, Tohru
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supporting information
p. 9837 - 9840
(2019/08/20)
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- Bio-inspired enantioselective total syntheses of (-)-viminalins A, B, H, I, and N and structural reassignment of (-)-viminalin M
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Bio-inspired enantioselective total syntheses of (-)-viminalins A, B, H, I, and N, isolated from the Myrtaceae family, were accomplished in a convergent fashion in 5, 5, 1, 1, and 3 steps, respectively. A highly regio- and diastereoselective oxidative [3 + 2] cycloaddition reaction of acylphloroglucinols with α-phellandrene, diastereoselective modified Friedel-Crafts reaction of acylphloroglucinols with piperetol, and stereoselective epoxidation of extremely hindered β-face were described as key reactions.
- Dethe, Dattatraya H.,Nirpal, Appasaheb K.
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p. 7507 - 7516
(2019/08/20)
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- Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes
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Enantioenriched, polycyclic compounds were obtained from a simple acylphloroglucinol scaffold. Highly enantioselective dearomatization was accomplished using a Trost ligand–palladium(0) complex. A computational DFT model was developed to rationalize observed enantioselectivities and revealed a key reactant-ligand hydrogen bonding interaction. Dearomatized products were used in visible light-mediated photocycloadditions and oxidative free radical cyclizations to obtain novel polycyclic chemotypes including tricyclo[4.3.1.01,4]decan-10-ones, bicyclo[3.2.1]octan-8-ones and highly substituted cycloheptanones.
- Hayashi, Mikayo,Brown, Lauren E.,Porco, John A.
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supporting information
p. 4800 - 4804
(2016/10/13)
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- NEW LIPOPHENOL COMPOUNDS AND USES THEREOF
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The present invention relates to a compound of formula (I) wherein: - i is 0 or 1; j is 0 or 1; k is 0 or 1; - R1 and R2 are in particular H, (C1-C12)alkyl, or a group of formula C(O)R; - R is a, linear or branched, alkyl radical, comprising at least 19 carbon atoms; - R3 is H and k=0 when j=1; or, when j=0, R3 is -C(O)R or -L-C(O)R; - L, U and L" are linkers; wherein, when j=0, at least one of the groups R1; R2 and R3 comprises a radical R.
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Page/Page column 41
(2015/11/10)
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- IRE-1α INHIBITORS
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PROBLEM TO BE SOLVED: To provide compounds which directly inhibit inositol requiring enzyme 1 (IRE-1α activity) in vitro, prodrugs, and pharmaceutically acceptable salts thereof. SOLUTION: The present invention provides a compound represented by formula (A) [R3 and R4 are H or the like; Q5-Q8, together with the benzene ring to which they are attached, form a benzofused ring, where at least one of Q5-Q8 is a heteroatom selected from N, O, and S. COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 1159; 1160
(2016/10/07)
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- Synthesis and evaluation of polyunsaturated fatty acid-phenol conjugates as anti-carbonyl-stress lipophenols
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Carbonyl and oxidative stress play a substantial role in various neurodegenerative diseases such as Alzheimer's Disease, Parkinsonism, and Age-related Macular Degeneration (AMD). In retinal pathologies, both mechanisms are involved in the transformation of all-trans-retinal (AtR, reactive aldehyde) into bis-retinoid A2E. Since an accumulation of AtR and A2E contributes to photoreceptor apoptosis, we designed and synthesized a series of O-alkylated resorcinol derivatives featuring enhanced anti-carbonyl-stress properties. Additionally, these phenolic structures are linked to a polyunsaturated fatty acid such as docosahexaenoic acid (C22:6 n-3; DHA) or to a lysophosphatidylcholine-DHA conjugate, in order to specifically increase their bioavailability, and thus, to target the retina. Selective syntheses of phloroglucinol-DHA, resveratrol-DHA, and phloroglucinol-DHA-PC (PC = phosphatidylcholine) conjugates using silyl protecting group strategies are presented, along with results of testing that demonstrate their ability to lower AtR toxicity in ARPE-19 cell lines. In order to use resorcinol derivatives to fight against the carbonyl-stress mechanism observed in retina pathologies, new lipophenol conjugates were synthesized with the aim of increasing bioavailability and reaching retina tissue. Strategies to link polyunsaturated fatty acids to polyphenol backbones are presented, along with the results of testing against retinal pigment epithelial cell lines. Copyright
- Crauste, Celine,Vigor, Claire,Brabet, Philippe,Picq, Madeleine,Lagarde, Michel,Hamel, Christian,Durand, Thierry,Vercauteren, Joseph
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p. 4548 - 4561
(2014/08/05)
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- Asymmetric, stereodivergent synthesis of (-)-clusianone utilizing a biomimetic cationic cyclization
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We report a stereodivergent, asymmetric total synthesis of (-)-clusianone in six steps from commercial materials. We implement a challenging cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms. Mechanistic studies point to the unique ability of formic acid to mediate the cyclization forming the clusianone framework. Aim for selectivity: (-)-Clusianone was produced by a stereodivergent asymmetric total synthesis in six steps from commercial materials. The synthesis utilizes a challenging formic acid-mediated cationic cyclization forging a bond between two sterically encumbered quaternary carbon atoms.
- Boyce, Jonathan H.,Porco, John A.
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supporting information
p. 7832 - 7837
(2014/08/05)
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- 1 -HYDROXY-BENZOOXABOROLES AS ANTIPARASITIC AGENTS
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Provided are compounds useful for controlling endoparasites both in animals and agriculture. Further provided are methods for controlling endoparasite infestations of an animal by administering an effective amount of a compound as described above, or a pharmaceutically acceptable salt thereof, to an animal, as well as formulations for controlling endoparasite infestations using the compounds described above or an acceptable salt thereof, and an acceptable carrier. The claimed compounds are described by the following Markush formula:A typical example for a compound according to above formula is: A typical example for a compound according to above formula is:
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Page/Page column 140-141
(2014/10/03)
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- Rapid synthesis of polyprenylated acylphloroglucinol analogs via dearomative conjunctive allylic annulation
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Polyprenylated acylphloroglucinols (PPAPs) are structurally complex natural products with promising biological activities. Herein, we present a biosynthesis-inspired, diversity-oriented synthesis approach for rapid construction of PPAP analogs via double decarboxylative allylation (DcA) of acylphloroglucinol scaffolds to access allyl-desoxyhumulones followed by dearomative conjunctive allylic alkylation (DCAA).
- Grenning, Alexander J.,Boyce, Jonathan H.,Porco, John A.
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supporting information
p. 11799 - 11804
(2014/10/16)
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- COMPOSITIONS COMPRISING STILBENE POLYPHENOL DERIVATIVES AND USE THEREOF FOR COMBATING THE AGEING OF LIVING ORGANISMS AND DISEASES AFFECTING SAME
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The invention relates to compositions comprising pholyphenol derivatives, characterised in that said polyphenols contain monomers, oligomers or polymers with units having formula (I), said units being characterised by the simultaneous presence of a resorcinol nucleus (nucleus A) and a para-phenol nucleus (nucleus B) which are interconnected by a carbon bond C, said derivatives being over-activated, in respect of the nucleophilic power thereof, by alkylation of at least one phenol function of each constituent monomer unit and stabilised by sterification by mixtures of fatty acids in proportions reflecting those of vegetable oils formed mainly by unsaturated fatty acids of all of the other phenol functions. The invention is suitable for use in cosmetics, dietetics and therapeutics.
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- PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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- Sulfur-substituted α-alkyl phenethylamines as selective and reversible MAO-A inhibitors: Biological activities, CoMFA analysis, and active site modeling
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A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-α methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds showed potent and selective MAO-A inhibitory activity (IC50 in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q2 of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.
- Gallardo-Godoy, Alejandra,Fierro, Angélica,McLean, Thomas H.,Castillo, Mariano,Cassels, Bruce K.,Reyes-Parada, Miguel,Nichols, David E.
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p. 2407 - 2419
(2007/10/03)
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- Biosynthesis of phloroglucinol
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Substantial concentrations of phloroglucinol were synthesized by Pseudomonas fluorescens Pf-5 expressing the plasmid-localized phlACBDE gene cluster responsible for biosynthesis of 2,4-diacetylphloroglucinol. Expression in Escherichia coli of a single gene in this cluster, P. fluorescens Pf-5 phlD, led to extracellular accumulation of phloroglucinol. Purification of PhlD to homogeneity afforded an enzyme that catalyzed the conversion of malonyl-CoA into phloroglucinol with Km = 5.6 μM and kcat = 10 min-1. Acetylase and deacetylase activities were observed with the catalyzed interconversions of phloroglucinol, 2-acetylphloroglucinol, and 2,4-diacetylphloroglucinol when phlACB was expressed in E. coli. Beyond the mechanistic implications attendant with the identification of an enzyme that catalyzes the conversion of malonyl-CoA into phloroglucinol, PhlD provides the basis for environmentally benign syntheses of phloroglucinol and resorcinol from glucose. Copyright
- Achkar, Jihane,Xian, Mo,Zhao, Huimin,Frost
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p. 5332 - 5333
(2007/10/03)
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- Deoxygenation of polyhydroxybenzenes: An alternative strategy for the benzene-free synthesis of aromatic chemicals
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New synthetic connections have been established between glucose and aromatic chemicals such as pyrogallol, hydroquinone, and resorcinol. The centerpiece of this approach is the removal of one oxygen atom from 1,2,3,4-tetrahydroxybenzene, hydroxyhydroquinone, and phloroglucinol methyl ether to form pyrogallol, hydroquinone, and resorcinol, respectively. Deoxygenations are accomplished by Rh-catalyzed hydrogenation of the starting polyhydroxybenzenes followed by acid-catalyzed dehydration of putative dihydro intermediates. Pyrogallol synthesis consists of converting glucose into myo-inositol, oxidation to myo-2-inosose, dehydration to 1,2,3,4-tetrahydroxybenzene, and deoxygenation to form pyrogallol. Synthesis of pyrogallol via myo-2-inosose requires 4 enzyme-catalyzed and 2 chemical steps. For comparison, synthesis of pyrogallol from glucose via gallic acid intermediacy and the shikimate pathway requires at least 20 enzyme-catalyzed steps. A new benzene-free synthesis of hydroquinone employs conversion of glucose into 2-deoxy-scyllo-inosose, dehydration of this inosose to hydroxyhydroquinone, and subsequent deoxygenation to form hydroquinone. Synthesis of hydroquinone via 2-deoxy-scyllo-inosose requires 2 enzyme-catalyzed and 2 chemical steps. By contrast, synthesis of hydroquinone using the shikimate pathway and intermediacy of quinic acid requires 18 enzyme-catalyzed steps and 1 chemical step. Methylation of triacetic acid lactone, cyclization, and regioselective deoxygenation of phloroglucinol methyl ether affords resorcinol. Given the ability to synthesize triacetic acid lactone from glucose, this constitutes the first benzene-free route for the synthesis of resorcinol. Copyright
- Hansen, Chad A.,Frost
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p. 5926 - 5927
(2007/10/03)
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- Bromophloroglucinols and their methyl ethers
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All 16 bromination products of phloroglucinol and its methyl ethers, as well as five bromoresorcinols and three of their dimethyl ethers, were synthesized and analyzed by nuclear magnetic resonance spectroscopy.Two or three equivalents of bromine convert phloroglucinol to di- and tribromophloroglucinol, 5-methoxyresorcinol to the tri- and 2,4-dibromo, 3,5-dimethoxyphenol to the tri- and 2,6-dibromo, and 1,3,5-trimethoxybenzene to the dibromo compound.With one equivalent of bromine, 3,5-dimethoxyphenol reacts preferentially at C-2 while 5-methoxyresorcinol gives both monobromo isomers.Partial debromination with sodium sulfite yields successively 2,4-dibromo- and 2-bromo-5-methoxyresorcinol from the tribromo compound but fails with brominated 3,5-dimethoxyphenol.In the resorcinol series, C-2 is invariably the least reactive position. 4,6-Dibromo-5-methoxyresorcinol and 2,4-dibromo-3,5-dimethoxyphenol are accessible by methylation of dibromophloroglucinol, obtained from 3,5-dibromo-2,4,6-trihydroxybenzoic acid by decarboxylation.In contrast to resorcinol and tribromoresorcinol, the partial bromination of pholoroglucinol and debromination of tribromopholoroglucinol are not selective.The 13Cnmr spectra of bromophloroglucinol methyl ethers show characteristic downfield shifts for methoxy groups orthogonal to the aromatic ring plane.
- Kiehlmann, E.,Lauener, R. W.
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p. 335 - 344
(2007/10/02)
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- Boron Trichloride as a Selective Demethylating Agent for Hindered Ethers: a Synthesis of the Phytoalexins α- and β-Pyrufuran, a Synthesis of Tri-O-methylleprolomin and its Demethylation
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Boron trichloride has been found to be an efficient reagent for the selective cleavage of sterically hindered methoxy groups in methoxyarenes.The scope and utility of this reaction are explored with examples drawn from derivatives of benzene, naphtalene, 9,10-dihydrophenanthrene and dibenzofuran.The method is applied to the synthesis of the phytoalexins α- (56) and β-pyrofuran (58) (1,3,4-trimethoxydibenzofuran-2-ol and 1,2,4-trimethoxydibenzofuran-3-ol).A synthesis of tri-O-methylleprolomin (61), a derivative of the unusual lichen metabolite leprolomin (60), is described and its demethylation with boron trichloride is studied.
- Carvalho, Christopher F.,Russo, Albert V.,Sargent, Melvyn V.
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p. 777 - 792
(2007/10/02)
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- Enol Ethers, XIV. Acylation of Keto Enol Ethers with Malonyl Dichloride - A New Synthesis of Phloroglucinols
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Phloroglucinols 4 and/or 4-hydroxy-2H-pyran-2-ones 5 are formed from keto enol ethers 1 and malonyl dichloride (2a) in high yields.Since the pyranones 5 can be smoothly converted into phloroglucinols, the reaction of 1 with 2a represents a new, facile synthetic route to phloroglucinols.The reaction proceeds via formation of a chloro carbonyl ketene 8 and its subsequent reaction with 1.The product ratio 4:5 is rationalized in terms of substituent effects in the enol ether substrate.
- Effenberger, Franz,Schoenwaelder, Karl-Heinz
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p. 3270 - 3279
(2007/10/02)
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- Boron Trichloride as a Selective Demethylating Agent for Hindered Ethers
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Boron trichloride has been found to be an efficient reagent for the selective cleavage of sterically hindered methoxy groups in methoxyarenes; the scope and utility of this reaction are explored.
- Carvalho, Christopher F.,Sargent, Melvyn V.
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p. 227 - 229
(2007/10/02)
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- MICRANTHOSIDE - A NEW GLYCOSIDE FROM Eupatorium micranthum
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From the epigeal parts of the plant Eupatorium micranthum Less., introduced into the Sukhumi Botanical Garden, a new glycoside has been isolated which has been called micranthoside and which has the structure of 4',5-di-O-β-glucosyl-7-O-methyldihydrokaempherol or 4',5-di-O-β-D-glucosyl-7-O-methylaromadendrin.
- Sagareishvili, T. G.,Alaniya, M. D.,Tsitsishvili, V. G.,Kemertelidze, E. P.
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p. 225 - 230
(2007/10/02)
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- Process for preparing polyphenols
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Polyphenols of the general formula: STR1 wherein R represents a readily cleavable ether group and R' represents a hydrogen atom or a lower alkoxycarbonyl, such as the methoxycarbonyl or ethoxycarbonyl group, and of phloroglucinol, are made by heating a compound of the general formula: STR2 wherein R and R' have the same significance given above, with an alkali metal alcoholate and, if desired, converting the resulting compound of formula I into pholoroglucinol by ether-cleavage and removal of any ester group denoted by R' which may be present in accordance with methods known per se.
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