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1.
Williams RM 《Chemical & pharmaceutical bulletin》2002,50(6):711-740
The syntheses and biosyntheses of the paraherquamide and brevianamide families of prenylated indole-derived alkaloids are reviewed. It has been proposed that the unique bicyclo[2.2.2]diazaoctan ring system that is common to this family of natural products, arises by a biological intramolecular Diels-Alder cycloaddition reaction. Both synthetic approaches and total syntheses of several members of this family of natural products are reviewed. The biosynthesis of these alkaloids has also constituted an active area of research and the current state of knowledge on the biosynthesis of these natural products are reviewed. 相似文献
2.
Dr. Amanda J Welford Dr. John J. Caldwell Dr. Manjuan Liu Meirion Richards Dr. Nathan Brown Dr. Cara Lomas Dr. Graham J. Tizzard Dr. Mateusz B. Pitak Dr. Simon J. Coles Prof. Suzanne A. Eccles Dr. Florence I. Raynaud Prof. Ian Collins 《Chemistry (Weinheim an der Bergstrasse, Germany)》2016,22(16):5657-5664
The 2,11‐cembranoid family of natural products has been used as inspiration for the synthesis of a structurally simplified, functionally diverse library of octahydroisobenzofuran‐based compounds designed to augment a typical medicinal chemistry library screen. Ring‐closing metathesis, lactonisation and SmI2‐mediated methods were exemplified and applied to the installation of a third ring to mimic the nine‐membered ring of the 2,11‐cembranoids. The library was assessed for aqueous solubility and permeability, with a chemical‐space analysis performed for comparison to the family of cembranoid natural products and a sample set of a screening library. Preliminary investigations in cancer cells showed that the simpler scaffolds could recapitulate the reported anti‐migratory activity of the natural products. 相似文献
3.
Angus Campbell Dr. Ian Mat Som Dr. Claire Wilson Prof. Dr. J. Stephen Clark 《Chemistry (Weinheim an der Bergstrasse, Germany)》2020,26(5):1155-1160
Six members of the asbestinin family of marine diterpene natural products have been synthesized in an efficient and stereoselective manner from a single oxa-bridged intermediate. Five of these natural products have not been synthesized previously and the structures of four of them have been confirmed as those proposed originally or following revisions to the original structures. The fifth natural product—asbestinin-21—has been shown to be a diastereomer of the compound that had been proposed previously. 相似文献
4.
Members of a family of alpha-methoxy-gamma-pyrone-containing polypropionate natural products have been stereoselectively synthesized. Two key iodovinyl pyrone building blocks were coupled to appropriately selected vinyl stannanes to assemble the highly substituted polyene side chains of the natural products. [structure: see text] 相似文献
5.
Dr. Erin N. Hancock Prof. M. Kevin Brown 《Chemistry (Weinheim an der Bergstrasse, Germany)》2021,27(2):565-576
The ladderane family of natural products are well known for their linearly concatenated cyclobutane skeletal structure. Owing to their unique carbocyclic framework, several chemical syntheses have been reported since their discovery in 2002. The focus of this review is to showcase the novel tactics that have been used to generate the ladderane core and the challenges that are associated with the synthesis of these unusual and complex natural products. 相似文献
6.
Although natural products containing a 1,2-oxazine ring are rare, more examples in this family of natural products have been
discovered since trichodermamides A and B were reported in 2003. In addition to their structural novelty, these natural products
possess very interesting bioactivities that are strongly dependent on their structures, making them attractive targets for
investigating structure-activity relationships (SAR). In this feature article, we summarized the methodologies developed in
recent years for constructing the 1,2-oxazine rings. Racemic and enantioselective total syntheses of trichodermamides A and
B, based on these methodologies, are reviewed in detail. 相似文献
7.
Tetronate antibiotics, a growing family of natural products featuring a characteristic tetronic acid moiety, are of importance and of particular interest for their typical structures, especially the spirotetronate structure, and corresponding versatile biological activities. Considerable efforts have persistently performed since the first tetronate was isolated, to elucidate the biosynthesis of natural tetronate products, by isotope-labeled feeding experiments, genetical characterization of biosynthetic gene clusters, and biochemical reconstitution of key enzymatic catalyzed reactions. Accordingly, the biosynthesis of spirotetronates has been gradually determined, including biosynthesis of a polyketide-derived backbone for spirotetronate aglycone, incorporation of a glycerol-derived three-carbon unit into tetronic acid moiety, formation of mature aglycone via Diels-Alder-like reaction, and decorations of aglycone with various deoxysugar moieties. In this paper, the biosynthetic investigations of natural tetronates are well documented and a common biosynthetic route for this group of natural products is summarized accordingly. 相似文献
8.
Hosea M. Nelson 《Tetrahedron letters》2009,50(15):1699-3691
Efforts toward the synthesis of the transtaganolide natural product family are described. A highly efficient Ireland-Claisen/Diels-Alder approach has been developed, which rapidly constructs the highly oxygenated and stereochemically rich core of these natural products. 相似文献
9.
Total Synthesis of (+/−)‐Frondosin B and (+/−)‐5‐epi‐Liphagal by Using a Concise (4+3) Cycloaddition Approach
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Duchan R. Laplace Bart Verbraeken Prof. Dr. Kristof Van Hecke Prof. Dr. Johan M. Winne 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(1):253-262
A recently developed (4+3) cycloaddition between dienes and furfuryl alcohols, as precursors of oxyallyl‐type cations, has been used as a key step in the racemic syntheses of two natural products: frondosin B and liphagal. This work demonstrates the synthetic potential of this cycloaddition reaction, and offers a short synthetic route to an interesting family of natural products. A full account of these synthetic studies is presented, further illustrating the mechanism, scope, and limitations of this straightforward synthetic method for seven‐membered rings. 相似文献
10.
Covering: 1957 to 2011. 3-Amino-5-hydroxy benzoic acid (3,5-AHBA) is a precursor for a large group of natural products, including the family of naphthalenic and benzenic ansamycins, the unique saliniketals, and the family of mitomycins. This review covers the biosynthesis of AHBA-derived natural products from a molecular genetics, chemical, and biochemical perspectives, and 174 references are cited. 相似文献
11.
12.
A synthesis of the core ring structure of the fargenin/fargenone family of natural products is presented. The general strategy is based upon biosynthetic speculation and exploits a cascade reaction, which transforms a spirocyclic dienone into the core ring system via a deprotonation-oxy-Michael-Wittig olefination sequence. This study represents the first synthesis work towards this family of natural products. 相似文献
13.
[reaction: see text] The catalytic diastereoselective Oshima-Utimoto reaction was employed for the construction of fraxinellone and related members of this limonoid family of natural products. After formation of the five-membered lactone, a stereoselective aldol reaction and olefin metathesis established the bicyclic ring system in the natural products. 相似文献
14.
Daniel A. Gubler 《Tetrahedron letters》2009,50(29):4265-4466
The tetracyclic core of the mitomycin family of natural products has been formed in one step from an acyclic precursor via a reductive aminocyclization reaction. Additionally, the eight-membered benzazocine can be prepared without the need for prior activation of the aniline. Construction of a mitomycin K analogue lacking the C9a methoxy moiety is also reported herein. 相似文献
15.
Gelatin, which is a soluble, natural polymer produced by partial hydrolysis of collagens, has been extensively used in food and pharmaceuticals. Donkey-hide gelatin is a well-known traditional Chinese medicine. The certification of donkey-hide gelatin is one of the most concerned issues for consumers. Currently, the source identification of the homologous family species, including donkey, horse and their hybrids, remains a major challenge. Here, three peptides (SGQPGTVGPAGVR, GASGPAGVR and GATGPAGVR) of the equine family species were screened using high-resolution LC-MS. The combination of these three peptides has been used as a high-performance marker in LC-MS/MS to identify the animal source (donkey, horse, and their hybrids) of donkey-hide-gelatin-containing products. Horse-hide gelatin and hybrid-hide gelatin can be detected in gelatin-based products even at very low percentages (0.05% and 0.10%, respectively). The marker peptide combination method is useful for source identification of homologous family species and is not only highly sensitive but also rapid. 相似文献
16.
[STRUCTURE: SEE TEXT] The ansamycin antibiotics contain metacyclophanic macrolactams, many of which possess potent antitumor activity. Only a few total syntheses of this family of natural products have been reported, and modifications to increase potency have not been described. Therefore, a method was developed to prepare the trienomycin A core via resin-bound triphenylphosphonium salts, which serve as both a reagent and a traceless linker to afford olefinic products that undergo ring-closing metathesis (RCM) to give macrocyclic scaffolds of varying ring sizes. 相似文献
17.
Echinomycin is the prototypical bisintercalator, a molecule that binds to DNA by inserting two planar chromophores between the base-pairs of duplex DNA, placing its cyclic depsipeptide backbone in the minor groove. As such, it has been the focus of an extensive number of investigations into its biological activity, nucleic acid binding and, to some extent, its structure-activity relationships. However, echinomycin is also the parent member of an extended family of natural products that interact with DNA by a similar mechanism of bisintercalation. The structural variety in these compounds leads to changes in sequence selectivity and and biological activity, particularly as anti-tumour and anti-viral agents. One of the more recently identified marine natural products that is moving close to clinical development is thiocoraline, and it therefore seems timely to review the various bisintercalator natural products. 相似文献
18.
Sandra Ainsua Martinez Martin Gillard Anne-Caroline Chany Jonathan W. Burton 《Tetrahedron》2018,74(38):5012-5021
The avenaciolide family of natural products are small α-methylene bis-γ-lactones that exhibit a wide variety of biological activities. Herein we report concise syntheses of five members of this family of natural products along with the synthesis of one non-natural analogue. The syntheses proceed in five or six steps from simple, commercially available compounds and feature a key oxidative cyclization/lactonization reaction that likely occurs via a radical mechanism. 相似文献
19.
Here we report the first total synthesis of violaceimides A–E, a family of sulfur-containing metabolites from Aspergillus violaceus, a sponge-associated fungus. A concise, convergent and enantioselective synthesis was developed for all five family members, from a common advanced intermediate. However, while the NMR spectral data matched that of the reported natural products, the optical rotations were of opposite sign. This result prompted the enantioselective synthesis of all four diastereomeric pairs of violaceimide E, and suggests that the stereochemistry might have been misassigned. 相似文献
20.
[reaction: see text] (+/-)-Mitorubrinic acid, a member of the azaphilone family of natural products, has been constructed in 12 steps. Key aspects of the synthesis include elaboration and oxidative dearomatization of an isocoumarin intermediate to provide the azaphilone nucleus with a disubstituted, unsaturated carboxylic acid side chain. 相似文献