Short synthesis of stenusine and norstenusine, two spreading alkaloids from Stenus beetles (Coleoptera: Staphylinidae)

Gedig, Thomas; Dettner, Konrad; Seifert, Karlheinz

doi:10.1016/j.tet.2007.01.024

Cited by 11 publications

(14 citation statements)

References 7 publications

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“…Finally, the key intermediate 2 was reacted with appropriate alkoxyamine/benzoxyamine under alkaline conditions to afford the target compound 3 . During the preparation of 3‐pyridylmethyl lithium, the reaction temperature is usually at −60 to −30°C; in our experiment, however, the temperature can be raised to 0°C (ice‐water bath), which makes the operation more convenient.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and biological activity of novel 2‐(pyridin‐3‐yl)ethan‐1‐one oxime ethers bearing adamantane moiety

Liu

Qian

Wan

et al. 2018

J Chinese Chemical Soc

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With the aim of discovering a lead compound for pyridine-based fungicide bearing adamantane moiety, a series of novel O-alkyl/benzyl-1-(adamantan-1-yl)-2-(pyridin-3-yl)ethan-1-one oximes were synthesized from 3-methylpyridine, ethyl (adamantan-1-yl)carboxylate, and alkoxyamine or benzoxyamine hydrochloride. The in vitro antifungal activity against four pathogenic fungi was evaluated, and some compounds exhibited good antifungal activity. Compounds 3d and 3f demonstrated strong activity against Sclerotinia sclerotiorum, with EC 50 values of 11.25 and 12.87 μg/mL, respectively; 3b, 3c, and 3k had notable activity against Botrytis cinerea, with EC 50 values of 12.78, 12.57, and 11.97 μg/mL, respectively. For Rhizoctonia Solani, 3d and 3g showed sufficient activity with EC 50 values of 9.66 and 8.90 μg/mL, respectively. In addition, 3d and 3g demonstrated moderate activity against Colletotrichum orbiculare, with EC 50 values of 14.32 and 15.83 μg/mL, respectively.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, and biological activity of novel 2‐(pyridin‐3‐yl)ethan‐1‐one oxime ethers bearing adamantane moiety

Liu

Qian

Wan

et al. 2018

J Chinese Chemical Soc

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“… Synthesis of ( R )‐ and ( S )‐norstenusine analogous to Scheme . Reagents and conditions: (a) LDA (lithium diisopropylamide), THF, 0 °C; 2‐bromopropane, THF, –78 °C → room temp., 81 %;10 (b) 52 %; (c) ( S )‐ 20 , 94 %; ( R )‐ 20 , 85 %; (d) ( R )‐ 21 , 81 %, 92 % ee ; ( S )‐ 21 , 80 %, 90 % ee . …”

Section: Resultsmentioning

confidence: 99%

“…The norstenusine isomers ( 21 ) were analogously prepared (Scheme ). The preparation of 3‐isobutylpyridine ( 18 ) was achieved starting from 3‐picoline ( 17 ) according to a known procedure (81 %) 10. Regioselective chlorination (52 %) and the coupling of auxiliaries 3 gave compounds 20 (94 %, 85 %) which were hydrogenated to the desired alkaloids 21 (81 %, 80 %) with ee values of 92 % ee [( R )‐ 21 ] and 90 % ee [( S )‐ 21 ].…”

Section: Resultsmentioning

confidence: 99%

“…The reason for these intrageneric differences is currently unknown. We tested the hypothesis that Stenus beetles impregnate the surface of their body with the pygidial gland secretion to defend themselves against microorganisms and found that the isomeric mixture of synthetic stenusine, similar to that of S. comma and (±)‐norstenusine,10 in concentrations occurring in nature, significantly inhibits the growth of bacteria ( Serratia entomophila ) and fungi ( Beauveria bassiana ) 11. A second function for this secretion, and thus of stenusine ( 1 ) and norstenusine ( 21 ), is that it acts as a deterrent against predators like Leptothorax platythorax ants, and this could be proven by feeding experiments 12.…”

Section: Introductionmentioning

confidence: 99%

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Straightforward Synthesis of All Stenusine and Norstenusine Stereoisomers

2011

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“…最后, 该酮肟与取代苯甲酸在 DCC/HOBt 作用下直接缩合生成目标化合物 3(合成路线见 Scheme 2). 在吡啶甲基锂的制备中, 文献报道反应温度一般在-30～-78 ℃ [15] , 但是在本实验中, 我们发现温度可以上升至-10～-15℃, 使操作更加方便. 此外, 我们采用肟与取代苯甲酸在 DCC/HOBt 催化下直接合成目标化合物, 收率在 90%～95%之间.…”

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Synthesis of Novel 3,3-Dimethyl-1-(pyridin-3-yl) butan-2-one Oxime Esters and Evaluation of Their Antifungal Activity

昝宁宁¹,

张钰镭²,

张帅³

et al. 2017

Chin. J. Org. Chem.

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A series of novel pyridine derivatives containing oxime esters have been synthesized from 3-methylpyridine, ethyl pivalate, hydroxylamine hydrochloride and substituted benzoic acid by addition, oximization and esterification reactions， which has the advantages of moderate reaction condition and high yield. Their structures were elucidated by IR, 1 H NMR, 13 C NMR and elemental analysis. Moreover, the target compounds were evaluated for their antifungal activity against two plant pathogens by the mycelium growth rate method. The results indicated that O-(4-bromobenzoyl)-3,3-dimethyl-1-(pyridin-3yl)butan-2-one oxime (3h) and O-(4-chlorobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3j) exhibited strong antifungal activity against S. sclerotiorum with EC 50 values of 5.07 and 4.81 µg/mL, and 3h, 3j and O-(3,4-dichlorobenzoyl)-3,3-dimethyl-1-(pyridin-3-yl)butan-2-one oxime (3l) displayed high antifungal activity against B. cinerea with EC 50 values of 4.98, 5.44 and 6.34 µg/mL, respectively.

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Short synthesis of stenusine and norstenusine, two spreading alkaloids from Stenus beetles (Coleoptera: Staphylinidae)

Cited by 11 publications

References 7 publications

Design, synthesis, and biological activity of novel 2‐(pyridin‐3‐yl)ethan‐1‐one oxime ethers bearing adamantane moiety

Design, synthesis, and biological activity of novel 2‐(pyridin‐3‐yl)ethan‐1‐one oxime ethers bearing adamantane moiety

Straightforward Synthesis of All Stenusine and Norstenusine Stereoisomers

Synthesis of Novel 3,3-Dimethyl-1-(pyridin-3-yl) butan-2-one Oxime Esters and Evaluation of Their Antifungal Activity

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