Synthesis of medium and large phostams, phostones, and phostines

• Jiaxi Xu

Beilstein J. Org. Chem. 2023, 19, 687–699, doi:10.3762/bjoc.19.50

• chemical synthesis of macrocyclic lactones which are the key structural motifs in some biologically active compounds, 14-methyl-2-phenoxy-1-oxa-2-phosphacyclotetradecane 2-oxide (74) was synthesized as the hapten from phenyl hydrogen (12-hydroxytridecyl)phosphonate (73) via Mitsunobu reaction. The

Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

• Angelique Ladwig,
• Markus Kroll and
• Stefan Schulz

Beilstein J. Org. Chem. 2023, 19, 167–175, doi:10.3762/bjoc.19.16

• used in chemical communication. Hyperolius cinnamomeoventris, a model species, possesses a gular gland on its vocal sac that emits chemicals, and sends visual and auditory signals during calling. Previous investigations have shown that the glandular compounds are typically macrocyclic lactones. However

• -isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol (R-14) as part of the semiochemical mixture released by gular glands of the African reed frog Hyperolius cinnamomeoventris. This establishes the importance of sesquiterpenes for reed frogs, alongside macrocyclic lactones [2]. The total

Anthelmintic drug discovery: target identification, screening methods and the role of open science

• Frederick A. Partridge,
• Ruth Forman,
• Carole J. R. Bataille,
• Graham M. Wynne,
• Marina Nick,
• Angela J. Russell,
• Kathryn J. Else and
• David B. Sattelle

Beilstein J. Org. Chem. 2020, 16, 1203–1224, doi:10.3762/bjoc.16.105

• cattle treated annually is hundreds of millions [1]. Treatment of horses, other equids, and companion animals is also a major use of anthelmintics. Anthelmintic drug discovery has been a continued emphasis in the animal health industry, driven by the spread of resistance to the macrocyclic lactones [2

• action of anthelmintic compounds, since it has been recognised that we do not fully understand how many anthelmintics work – for example the concentrations of macrocyclic lactones that paralyse worms in vitro are much greater than the concentration achieved by effective doses in vivo [147]. Several

Preparation, structure, and reactivity of bicyclic benziodazole: a new hypervalent iodine heterocycle

• Akira Yoshimura,
• Michael T. Shea,
• Cody L. Makitalo,
• Melissa E. Jarvi,
• Gregory T. Rohde,
• Akio Saito,
• Mekhman S. Yusubov and
• Viktor V. Zhdankin

Beilstein J. Org. Chem. 2018, 14, 1016–1020, doi:10.3762/bjoc.14.87

• preparation of several bicyclic benziodoxoles 3 starting from 2-iodoisophthalic acid (2, Scheme 1b). These bicyclic benziodoxoles 3 can be used as efficient coupling reagents for the direct condensation reaction between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, or amides

Identification, synthesis and mass spectrometry of a macrolide from the African reed frog Hyperolius cinnamomeoventris

• Markus Menke,
• Pardha Saradhi Peram,
• Iris Starnberger,
• Walter Hödl,
• Gregory F.M. Jongsma,
• David C. Blackburn,
• Mark-Oliver Rödel,
• Miguel Vences and
• Stefan Schulz

Beilstein J. Org. Chem. 2016, 12, 2731–2738, doi:10.3762/bjoc.12.269

• , is usually not possible from an EI mass spectrum. In the article, we present the synthesis and for the first time elucidate the structure of macrolides from the frog family Hyperoliidae. Keywords: chemical communication; chiral gas chromatography; macrocyclic lactones; ring-closing metathesis

• ; pheromones; Introduction The lactone motif is found in many compounds that are used in chemical communication. Among them, macrocyclic lactones are an important class because of their biosynthetic availability and their inherent compound properties. During the biosynthesis of macrocyclic lactones, a fatty

• from Madagascar also use chemical cues. Macrocyclic lactones such as phoracantholide I (3), phoracantholide J (4) or gephyromantolide A (5), are released by males from femoral glands to serve as signals, often accompanied by secondary alcohols (Figure 1) [2][3][4]. Another frog family most likely using

Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides

• Franziska Hemmerling and
• Frank Hahn

Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148

• the respective heterocycles. We will not cover medium-sized and macrocyclic lactones and lactams, but concentrate on small heterocycles with ring sizes between 3 and 6 atoms (for a review about macrolactones see reference [12]). Review 1 Oxygen-containing heterocycles Oxygen-containing heterocycles

Formation of macrocyclic lactones in the Paternò–Büchi dimerization reaction

• Junya Arimura,
• Tsutomu Mizuta,
• Yoshikazu Hiraga and
• Manabu Abe

Beilstein J. Org. Chem. 2011, 7, 265–269, doi:10.3762/bjoc.7.35

• of macrocyclic lactones. To investigate the effects of concentration, solvent, and temperature on the formation of 2a, the photochemical reaction of 1a was conducted under the variety of conditions (Table 1). The yield of intermolecular product 2a was expected to be improved when the concentration of

• on the yield of 2a (entries 7–9). In summary, the intramolecular products such as A and B were not observed in the photochemical reaction of furan derivatives 1a,b, but interestingly the Paternò–Büchi dimers 2a,b with the Ci symmetry, i.e., macrocyclic lactones, were isolated in ca. 20% yield. The

• to give the observed macrocyclic lactones 2. This finding should stimulate future experimental and computational studies on the mechanistically and synthetically fascinating formation of macrocyclic lactone derivatives. Experimental NMR and MS measurements were made using JEOL JMN-LA500 and Thermo