A Short Synthesis of (±)-Matrine

Boiteau, Laurent; Boivin, Jean; Liard, Annie; Quiclet‐Sire, Béatrice; Zard, Samir Z.

doi:10.1002/(sici)1521-3773(19980504)37:8<1128::aid-anie1128>3.0.co;2-p

Cited by 70 publications

(27 citation statements)

References 3 publications

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“…An alternative approach is to couple a source of radical with a strong hydrogen donor, such as a peroxide initiator and a secondary alcohol. Peroxides can induce radical cleavage of the C S bond of a thiocarbonylthio group to generate a radical intermediate, which can undergo either intramolecular cyclization or intermolecular addition, depending on the conditions [85]. By performing the reaction in the presence of secondary alcohol, the radical formed from the fragmentation of the polymeric chains from the RAFT intermediate can be trapped by a hydrogen atom from the alcohol.…”

Section: Radical-induced End-group Removalsupporting

confidence: 93%

Polymers with Well‐Defined End Groups via RAFT – Synthesis, Applications and Post modifications

Barner

Perrier

2008

Handbook of RAFT Polymerization

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Section: Radical-induced End-group Removalsupporting

confidence: 93%

Polymers with Well‐Defined End Groups via RAFT – Synthesis, Applications and Post modifications

Barner

Perrier

2008

Handbook of RAFT Polymerization

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“…6) Due to its notable medicinal efficacy, attempts to synthesize and biosynthesize matrine were conducted. [7][8][9] In 1995, Saito et al proposed the biosynthetic pathway of the carbon framework of matrine. 10) Although the first steps of quinolizidine alkaloids biosynthesis have been elucidated recently in S. flavescens, 11) more effort needs to be done to puzzle out the practical biosynthetic pathway of matrine.…”

Section: Sophora Flavescens Aiton Kuraramentioning

confidence: 99%

Transcriptome Analysis of Nine Tissues to Discover Genes Involved in the Biosynthesis of Active Ingredients in <i>Sophora flavescens</i>

Han

Takahashi

Nakamura

et al. 2015

Biological & Pharmaceutical Bulletin

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Sophora flavescens AITON kurara, has long been used to treat various diseases. Although several research findings revealed the biosynthetic pathways of its characteristic chemical components as represented by matrine, insufficient analysis of transcriptome data hampered in-depth analysis of the underlying putative genes responsible for the biosynthesis of pharmaceutical chemical components. In this study, more than 200 million fastq format reads were generated by Illumina's next-generation sequencing approach using nine types of tissue from S. flavescens, followed by CLC de novo assembly, ultimately yielding 83325 contigs in total. By mapping the reads back to the contigs, reads per kilobase of the transcript per million mapped reads values were calculated to demonstrate gene expression levels, and overrepresented gene ontology terms were evaluated using Fisher's exact test. In search of the putative genes relevant to essential metabolic pathways, all 1350 unique enzyme commission numbers were used to map pathways against the Kyoto Encyclopedia of Genes and Genomes. By analyzing expression patterns, we proposed some candidate genes involved in the biosynthesis of isoflavonoids and quinolizidine alkaloids. Adopting RNA-Seq analysis, we obtained substantially credible contigs for downstream work. The preferential expression of the gene for putative lysine/ornithine decarboxylase committed in the initial step of matrine biosynthesis in leaves and stems was confirmed in semi-quantitative polymerase chain reaction (PCR) analysis. The findings in this report may serve as a stepping-stone for further research into this promising medicinal plant.Key words Sophora flavescens; RNA-Seq analysis; biosynthesis; quinolizidine alkaloid; isoflavonoid Sophora flavescens AITON kurara, has been recorded and used for more than 1800 years. 1) As a widely distributed and effective herbal medicine, it severed as a cure for asthma, sores, gastrointestinal hemorrhage, diarrhea, allergy, inflammation in eastern Asian countries.2,3) Main chemical components of S. flavescens include flavonoids (1.5%), alkaloids (3.3%), alkylxanthones, quinones, triterpene glycosides, fatty acids as well as essential oils and recently, several clinical studies reported that alkaloids of S. flavescens were efficacious in treating various types of solid tumors (including breast, lung, liver and gastrointestinal tract cancers), which drew close attention to this traditional herbal plant. 1,4) In 1889, the characteristic compound matrine was isolated from the dry roots of S. flavescens by Nagai 5) and then in 1966, Okuda et al. confirmed the absolute structure of (+)-matrine.6) Due to its notable medicinal efficacy, attempts to synthesize and biosynthesize matrine were conducted. [7][8][9] In 1995, Saito et al. proposed the biosynthetic pathway of the carbon framework of matrine. 10) Although the first steps of quinolizidine alkaloids biosynthesis have been elucidated recently in S. flavescens, 11) more effort needs to be done to puzzle out the practical biosyn...

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“…This is demonstrated by the key step in the total synthesis of matrine ( 43 ), which starts with readily available alkene 38 and xanthate 39 , and implies one intermolecular addition followed by two successive cyclisations [26]. Two isomeric tetracyclic compounds 41a and 41b as well as simple addition product 40 are thus obtained in good combined yield (Scheme 9).…”

Section: Reviewmentioning

confidence: 99%

Some aspects of radical chemistry in the assembly of complex molecular architectures

Quiclet‐Sire¹,

Zard²

2013

Beilstein J. Org. Chem.

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SummaryThis review article describes briefly some of the radical processes developed in the authors’ laboratory as they pertain to the concise assembly of complex molecular scaffolds. The emphasis is placed on the use of nitrogen-centred radicals, on the degenerate addition–transfer of xanthates, especially on its potential for intermolecular carbon–carbon bond formation, and on the generation and capture of radicals through electron transfer processes.

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A Short Synthesis of (±)-Matrine

Abstract: Three different radical reactions were used in a short total synthesis of (±)-matrine (1). Two of the four six-membered rings and four new bonds were created in one radical cascade involving intermolecular addition followed by two successive cyclizations and transfer of a xanthate group.

Cited by 70 publications

References 3 publications

Polymers with Well‐Defined End Groups via RAFT – Synthesis, Applications and Post modifications

Polymers with Well‐Defined End Groups via RAFT – Synthesis, Applications and Post modifications

Transcriptome Analysis of Nine Tissues to Discover Genes Involved in the Biosynthesis of Active Ingredients in <i>Sophora flavescens</i>

Some aspects of radical chemistry in the assembly of complex molecular architectures

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