Second‐Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment

Boyer, Alistair; Veitch, Gemma E.; Beckmann, Edith; Ley, Steven V.

doi:10.1002/ange.200805395

Cited by 12 publications

(3 citation statements)

References 48 publications

(15 reference statements)

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“…The complete synthesis of azadirachtin required 71 steps, resulting in a yield of 0.00015% [6] . Boyer et al [111] managed to reduce the number of steps to 62 by enhancing the synthesis route but remained far from meeting the fundamental requirements for large-scale azadirachtin production. Currently, plant-derived azadirachtin is the preferred choice for biotesting and field applications.…”

Section: Access To Azadirachtin and The Gap Between Supply And Demandmentioning

confidence: 99%

A comprehensive review of azadirachtin: physicochemical properties, bioactivities, production, and biosynthesis

Su,

Liang,

Xue

et al. 2023

Acupuncture and Herbal Medicine

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Azadirachtin, a complex tetratriterpenoid limonin with potent insecticidal properties, is the most widely used biological pesticide worldwide. Its versatile pharmacological applications include the inhibition of tumor growth and anti-malarial, anti-bacterial, and anti-inflammatory properties. Azadirachtin plays a pivotal role in pest control and novel drug development. The primary source of azadirachtin is the neem tree (Azadirachta indica A. Juss), with an azadirachtin content ranging from 0.3% to 0.5%. Despite the market demand for botanical pesticides reaching approximately 100,000 tons per year, the annual neem production in China is only 1.14 tons. Although azadirachtin can be obtained through plant extraction or chemical synthesis, the quantity obtained does not meet the market demand in China. The sluggish pace of azadirachtin biosynthesis results from the limited availability of genetic information and the complexity of the synthetic pathway. Recent advancements in azadirachtin biosynthesis hold promise as an efficient collection method. In this study, we explored the physicochemical properties, biological activities, mechanisms of action, and acquisition methods of azadirachtin. We also delved into recent progress in azadirachtin biosynthesis and assessed potential future usage challenges. This study aims to establish a theoretical foundation for the scientific application and efficient synthesis of azadirachtin, offering valuable reference information to the industry.

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Section: Access To Azadirachtin and The Gap Between Supply And Demandmentioning

confidence: 99%

A comprehensive review of azadirachtin: physicochemical properties, bioactivities, production, and biosynthesis

Su,

Liang,

Xue

et al. 2023

Acupuncture and Herbal Medicine

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“…During synthesis of the antifeedant and growthdisruption agent azadirachtin it was used for a lactol to lactone conversion [192][193][194][195][196], and for a step in synthesis of the agonist dysiherbaine [197]. The non-proteinogenic amino acid anticapsin was made using TPAP/NMO/PMS/CH 3 CN (Fig.…”

Section: Natural Product/pharmaceutical Syntheses Involving Secondarymentioning

confidence: 99%

Oxidation of Alcohols, Carbohydrates and Diols

Griffith

2009

Catalysis by Metal Complexes

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This is one of the most important classes of oxidation effected by Ru complexes, particularly by RuO 4 , [RuO 4 ] − , [RuO 4 ] 2− and RuCl 2 (PPh 3 ) 3 , though in fact most Ru oxidants effect these transformations. The chapter covers oxidation of primary alcohols to aldehydes (section 2.1), and to carboxylic acids (2.2), and of secondary alcohols to ketones (2.3). Oxidation of primary and secondary alcohol functionalities in carbohydrates (sugars) is dealt with in section 2.4, then oxidation of diols and polyols to lactones and acids (2.5). Finally there is a short section on miscellaneous alcohol oxidations in section 2.6.In this chapter the first of the two most important categories of oxidations catalysed by Ru complexes (the other being alkene and alkyne oxidations in Chapter 3) are considered. The approach in this and subsequent chapters differs from that of Chapter 1, concentrating here on the substrate rather than on the oxidant. The text is divided into the categories of alcohols and their oxidations. There are summaries in section 2.3.6 of systems of limited applicability which are mentioned only in Chapter 1, and in section 2.3.7 of large-scale (>1 g) oxidations.The first oxidations of alcohols by stoicheiometric RuO 4 /H 2 O were reported in 1958, of primary alcohols to aldehydes or carboxylic acids and secondary alcohols to ketones [1]. The first Ru-catalysed oxidation of an alcohol was reported in 1965 when Parikh and Jones used RuO 2 /aq. Na(IO 4 )/CCl 4 1 ( Table 2.3) [2] to oxidise secondary alcohol groups in carbohydrates.Oxidation of alcohols is the most frequently reviewed topic for Ru-catalysed oxidations [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Mechanisms of alcohol oxidation by Ru complexes have been reviewed [21].

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“…It is chemically interesting because of its complex structure and its synthesis challenge, which required 18 years to identify its chemical structure and another 22 years to identify its synthesis (Morgan, ). Although this compound is a tetranortriterpenoid with 16 chiral carbon centers, researchers have devoted to develop a suitable method for total synthesis of azadirachtin (Ley, ; Veitch et al., ; Devakumar and Kumar, ; Boyer et al., ; Nakagawa et al., ), which shows tremendous commercialization potential for insect pest control.…”

Section: Introductionmentioning

confidence: 99%

A COMPREHENSIVE STUDY ON APOPTOSIS INDUCTION BY AZADIRACHTIN IN Spodoptera frugiperda CULTURED CELL LINE Sf9

Shu

Wang

et al. 2015

Arch Insect Biochem Physiol

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The induction of apoptosis by azadirachtin, a well-known botanical tetranortriterpenoid isolated from the neem tree (Azadirachta indica A. Juss) and other members of the Meliaceae, was investigated in Spodoptera frugiperda cultured cell line (Sf9). Morphological changes in Sf9 cells treated by various concentrations of azadirachtin were observed at different times under light microscopy. Morphological and biochemical analysis indicated that Sf9 cells treated by 1.5 μg/mL azadirachtin showed typical morphological changes, which were indicative of apoptosis and a clear DNA ladder. The flow cytometry analysis showed the apoptosis rate reached a maximum value of 32.66% at 24 h with 1.5 μg/mL azadirachtin in Sf9 cells. The inhibition of Sf9 cell proliferation suggested that the effect of azadirachtin was dose dependent and the EC50 at 48 and 72 h was 2.727 × 10(-6) and 6.348 × 10(-9) μg/mL, respectively. The treatment of azadirachtin in Sf9 cells could significantly increase the activity of Sf caspase-1, but showed no effect on the activity of Topo I, suggesting that the apoptosis induced by azadirachtinin Sf9 cells is through caspase-dependent pathway. These results provided not only a series of morphological, biochemical, and toxicological comprehensive evidences for induction of apoptosis by azadirachtin, but also a reference model for screening insect cell apoptosis inducers from natural compounds.

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Second‐Generation Synthesis of Azadirachtin: A Concise Preparation of the Propargylic Mesylate Fragment

Cited by 12 publications

References 48 publications

A comprehensive review of azadirachtin: physicochemical properties, bioactivities, production, and biosynthesis

A comprehensive review of azadirachtin: physicochemical properties, bioactivities, production, and biosynthesis

Oxidation of Alcohols, Carbohydrates and Diols

A COMPREHENSIVE STUDY ON APOPTOSIS INDUCTION BY AZADIRACHTIN IN Spodoptera frugiperda CULTURED CELL LINE Sf9

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