99315-76-1Relevant articles and documents
Synthesis method of jatrophane type diterpene key intermediate and derivatives thereof
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Paragraph 0112-0113, (2021/02/06)
The invention discloses a synthesis method of a jatrophane type diterpene key intermediate and derivatives thereof. The structural formula of the key intermediate is shown in multiple embodiments of the invention, and the jatrophane type diterpene key int
Stereoselective Construction of the Methylcyclopentane Core of Peditithins B-H with Five Continuous Stereocenters
Li, Qingjiang,Li, Wei,Ni, Fu-Qiang,Wu, Shu-Qi,Yin, Sheng
, p. 9360 - 9364 (2020/12/21)
A stereoselective construction of the methylcyclopentane core (3) of jatrophane diterpenoids peditithins B-H was achieved in 14 steps from commercially available d-(+)-ribono-1,4-lactone (9). The linear 5-ene-heptanal derived from 9 was cyclized to the five-membered ring by an intramolecular carbonyl ene reaction, and five continuous stereocenters on 3 were stereoselectively introduced via a successive substrate-controlled manner, involving diastereoselective 1,4-addition, MoOPH-induced hydroxylation, and stereospecific epoxidation.
High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues
Moreaux, Maxime,Bonneau, Guillaume,Peru, Aurélien,Brunissen, Fanny,Janvier, Marine,Haudrechy, Arnaud,Allais, Florent
, p. 1600 - 1604 (2019/01/14)
A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.
NOVEL 3-SUBSTITUTED 5-AMINO-6H-THIAZOLO[4,5-D]PYRIMIDINE-2,7-DIONE COMPOUNDS FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION
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, (2016/08/07)
The present invention relates to compounds of formula (I), wherein R1, R2 and R3 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.
NOVEL SUBSTITUTED AMINOTHIAZOLOPYRIMIDINEDIONE FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION
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, (2016/11/28)
The present invention relates to compounds of formula (I), wherein R1 to R5 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.
Exploring the Chemistry of Bicyclic Isoxazolidines for the Multicomponent Synthesis of Glycomimetic Building Blocks
Hoogenboom, Jorin,Lutz, Martin,Zuilhof, Han,Wennekes, Tom
, p. 8826 - 8836 (2016/10/14)
Starting from a chiral furanone, the nitrone-olefin [3 + 2] cycloaddition can be used to obtain bicyclic isoxazolidines for which we report a set of reactions to selectively modify each functional position. These synthetically versatile bicyclic isoxazolidines allowed us to obtain complex glycomimetic building blocks, like iminosugars, via multicomponent chemistry. For example, a library of 20 pipecolic acid derivatives, a recurring motif in various prescription drugs, could be obtained via a one-pot Staudinger/aza-Wittig/Ugi three-component reaction of a bicyclic isoxazolidine-derived azido-hemiacetal. Notably, specific pipecolic acids in this library were obtained via hydrolysis of an unique tricyclic imidate side product of the Ugi reaction. The azido-hemiacetal was also converted into an aza-C-glycoside iminosugar via an unprecendented one-pot Staudinger/aza-Wittig/Mannich reaction.
Synthesis and Evaluation of a 2,11-Cembranoid-Inspired Library
Welford, Amanda J,Caldwell, John J.,Liu, Manjuan,Richards, Meirion,Brown, Nathan,Lomas, Cara,Tizzard, Graham J.,Pitak, Mateusz B.,Coles, Simon J.,Eccles, Suzanne A.,Raynaud, Florence I.,Collins, Ian
supporting information, p. 5657 - 5664 (2016/04/20)
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. Building a bridge: A library of compounds based on the naturally occurring 2,11-cembranoid family has been synthesised by using different synthetic strategies. The library was found to cover the space between the natural products and a screening library sample set (see figure). The new compounds were shown to recapitulate reported activities of the natural products.
Novel Bicyclic Pyridinones
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Page/Page column, (2014/04/03)
Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.
An approach to the carbon backbone of bielschowskysin, part 1: Photocyclization strategy
Himmelbauer, Martin,Farcet, Jean-Baptiste,Gagnepain, Julien,Mulzer, Johann
, p. 8214 - 8244 (2014/01/06)
Several macrocyclization reaction attempts of highly advanced precursors toward a total synthesis of marine diterpene bielschowskysin are disclosed. Biomimetic [2+2]-photocyclization reactions were applied to construct the cyclobutane core in these intermediates, which could be accessed along scalable high-yielding reaction sequences from cheap enantiopure starting-materials. Asymmetric syntheses of various highly functionalized intermediates toward the total synthesis of bielschowskysin (1) are described. In particular a biomimetic [2+2]-photocycloaddition reaction strategy, forming the cyclobutane core, was followed by various macrocyclization reactions attempts. Copyright
Expedient pathway into optically active 2-oxopiperidines
Van Den Broek, Sebastiaan A. M. W.,Rensen, Peter G. W.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
scheme or table, p. 5906 - 5912 (2011/01/12)
The piperidine ring system is one of the most common structural subunits and is found in many natural products. Moreover, piperidine alkaloids and derivatives thereof are of great interest for the pharmaceutical industry since they exhibit a wide range of
