(m.n)-Homorubins: syntheses and structures

Pfeiffer, William P.; Lightner, David A.

doi:10.1007/s00706-014-1288-4

Cited by 5 publications

(4 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Under a hydrogen atmosphere, to a stirred solution of platinum(IV) oxide (PtO 2 ) 0.018 g (20%) in methanol (5 mL), a solution of 2a (0.3044 g, 2 mmol) in methanol (1 mL) was added slowly at 0 °C. The reaction mixture was maintained for 1–3 h at 25 °C 28,29 . The mixture was filtered through a celite pad, followed by addition of palladium on carbon (10%) (0.01 eq) into organic phases at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

“…The cross‐coupling reaction between the racemic synthon 1b and 1‐bromopent‐1‐yn‐3‐ol to give the product 2b (81% yield). Product 2b was then reduced to obtain 3b (95% yield) by hydrogenation with PtO 2 28,29 or palladium on carbon, 27 followed by esterification (95% yield) of 3b with butyryl chloride to obtain the final product 4b (overall 73% yield). 1 H‐NMR (400 MHz, CDCl 3 ) δ 4.91–4.82 (m, 1H, CH 2 CHCH 3 ), 4.82–4.74 (m, 1H, CH 2 CHCH 3 ), 2.28–2.19 (m, 4H, CH 2 ), 1.71–1.56 (m, 4H, CH 2 ), 1.56–1.39 (m, 6H, CH 2 ), 1.37–1.20 (m, 4H, CH 2 ), 1.16 (d, J = 6.1 Hz, 3H, CH 3 ), 0.97–0.88 (m, 6H, CH 2 ), 0.84 (t, J = 7.4 Hz, 3H, CH 3 ).…”

Section: Methodsmentioning

confidence: 99%

“…The reaction mixture was maintained for 1-3 h at 25 °C. 28,29 The mixture was filtered through a celite pad, followed by addition of palladium on carbon (10%) (0.01 eq) into organic phases at 0 °C. The reaction proceeded for another 1-3 h at 25 °C under hydrogen and monitored with thin layer chromatography (TLC).…”

Section: Synthesis Of (2s7smentioning

confidence: 99%

See 2 more Smart Citations

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

et al. 2022

Pest Management Science

View full text Add to dashboard Cite

BACKGROUND: Sudden outbreaks of the orange wheat blossom midge, Sitodiplosis mosellana (Géhin) cause huge wheat yield losses. Use of sex pheromones is more efficient than laborious egg counting to monitor these hidden-concealed insects. Quick synthesis of the sex pheromones is therefore required to meet the sudden outbreak needs. RESULTS: A synthetic approach of stereospecific and racemic S. mosellana pheromones was presented. This method afforded the stereospecific and racemic S. mosellana pheromones in three steps and high enantioselectivity (> 98% ee for (2S,7S)-2,7-nonanediyl dibutyrate) in less than 1 day with 74% and 73% overall yields, respectively, whereas most conventional methods require longer synthesis time with less than 40% yield. The synthesis routes could quickly and economically afford the pheromones, starting from synthon (S)-but-3-yn-2-ol (1a) or but-3-yn-2-ol (1b), through the same three-step processes of coupling, reduction, and esterification. The Y-tube olfactometer results showed significant attractiveness of the synthetic stereospecific and racemic sex pheromones to S. mosellana males relative to the blank control (P < 0.001). Field trials also demonstrated significant attractiveness of the synthetic stereospecific and racemic sex pheromones relative to the blank control (P < 0.001).CONCLUSION: This modular approach is conducive to the deployment of field traps and timely responses to S. mosellana outbreaks and can be a time-saving and cost-effective tool to manage S. mosellana.

show abstract

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

et al. 2022

Pest Management Science

View full text Add to dashboard Cite

show abstract

“…Polyynes which contain pyrrole end-groups are a very scanty class of compounds. To the best of our knowledge, only butadiynes are known to date, among which there are porphyrinoids with butadiyne chains incorporated into a macrocycle skeleton or modified bilirubins . For instance, Vogel and Panda published the synthesis of a very physicochemically interesting 26π–β-octasubstituted diacetylene-cumulene porphycene from butadiyne-bridged bipyrroledialdehydes.…”

Section: Introductionmentioning

confidence: 99%

Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles

et al. 2016

View full text Add to dashboard Cite

In this contribution, the synthesis of long chain hexatriynyl- and octatetraynyl-substituted pyrroles in one step from 1-halopolyyne precursors is reported. The products were obtained via a mechanochemical approach by simple grinding of 1-haloalkynes with N-substituted pyrroles and potassium carbonate which played a role of heterogeneous catalyst and this solvent- and transition metal-free approach is unprecedent in the synthesis of new, organic, long chain polyynes. Additionally, an extensive X-ray single crystal study of pyrrole end-capped polyynes is presented. Such compounds are possible substrates for different oligoheterocycles and have a significant application potential such as for instance molecular wires.

show abstract

Three bilindione isomers: synthesis, characterization and reactivity of biliverdin analogs

Wang

Sun

et al. 2017

J Biol Inorg Chem

View full text Add to dashboard Cite

Linear tetrapyrrole is the core structure of light-sensitive native cofactors such as phycocyanobilin, phytochromobilin and bile pigments, which attracts increasing attention in biomimetic chemistry, photochemistry and coordination chemistry. To decipher the relationship between structures and functions, in this work, we firstly reported the synthesis, isolation and characterization of three bilindione isomers (ZZZ, syn, syn, syn 1, EZE, syn, syn, anti 2 and EZE, anti, syn, anti 3) bearing meso-pentafluorophenyl groups. The structures were confirmed by X-ray diffraction and 2-D NMR spectroscopes. More importantly, the interconversion between three isomers under heating and light irradiation was investigated, and isomer 3 was found to be transformed to 1 and 2 more easily, which is in line with the results of DFT calculation. This work provides important insights for understanding the relationship between structures and functions and would be important to further construct metal complexes based on linear tetrapyrrole ligands, which are complementary to well-studied the cyclic analogs such as porphyrin and corroles.

show abstract

(m.n)-Homorubins: syntheses and structures

Cited by 5 publications

References 42 publications

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

Modular synthesis of the pheromone (2S,7S)‐2,7‐nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Géhin) (Diptera: Cecidomyiidae)

Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles

Three bilindione isomers: synthesis, characterization and reactivity of biliverdin analogs

Contact Info

Product

Resources

About