Regio- and Stereochemical Study of Sex Pheromone of Pine Sawfly; <i>Diprion</i>  <i>nipponica</i>

Tai, Akira; Syouno, Emi; Tanaka, Kazuki; Fujita, Morifumi; Sügimura, Takashi; Higashiura, Yasutomo; Kakizaki, Masashi; Hara, Hideho; Naito, Tikahiko

doi:10.1246/bcsj.75.111

Cited by 23 publications

(9 citation statements)

References 19 publications

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“… Synthesis of bromides. Reagents and conditions: a) TsCl/Py/0 °C/18 h;30–31 b) LiBr/DMF/20 °C/5 h;30 c) allylmagnesium bromide/Et 2 O/20 °C/2 weeks;32–33 d) 1. B 2 H 6 /THF/0 °C/30 min/20 °C/1 h; 2.…”

Section: Resultsmentioning

confidence: 99%

Volatile Lactones — (5S,S)‐5‐Methyl‐3‐(methylalkyl)furan‐2(5H)‐ones — Identified in the Submerged Cultivation of Streptomyces Avermitilis

Řezanka¹,

Sigler²

2006

Eur J Org Chem

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Six new compounds have been identified in the volatile fractions produced during the submerged cultivation of Streptomyces avermitilis. By recording the GC/MS, GC/FTIR, CD, 1H and 13C NMR data and by performing chemical degradation experiments, these compounds were determined to be (5S,S)‐5‐methyl‐3‐(methylalkyl)furan‐2(5H)‐ones. Herein, the existence of volatile lactones with an anteiso structure of the side‐chain is thus documented for the first time. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Section: Resultsmentioning

confidence: 99%

Volatile Lactones — (5S,S)‐5‐Methyl‐3‐(methylalkyl)furan‐2(5H)‐ones — Identified in the Submerged Cultivation of Streptomyces Avermitilis

Řezanka¹,

Sigler²

2006

Eur J Org Chem

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“…[21] Briefly, MeOH was injected into a solution of conjugate 1 in CHCl 3 (0.5 mm) to obtain a solution with a CHCl 3 /MeOH ratio of 1:3 v/v in a small flask. [21] Briefly, MeOH was injected into a solution of conjugate 1 in CHCl 3 (0.5 mm) to obtain a solution with a CHCl 3 /MeOH ratio of 1:3 v/v in a small flask.…”

Section: Methodsmentioning

confidence: 99%

“…The self-assembled nanostructures fabricated from compounds 1 and 2 were prepared by the solution-mixture method. [21] Briefly, MeOH was injected into a solution of conjugate 1 in CHCl 3 (0.5 mm) to obtain a solution with a CHCl 3 /MeOH ratio of 1:3 v/v in a small flask. After the solution was allowed to equilibrate at ambient temperature for approximately 4 days, the loose aggregates were observed.…”

Section: Nanostructure Fabricationmentioning

confidence: 99%

Helical Self‐Assembly of Optically Active Phthalocyanine Derivatives: Effect of ZnO Coordination Bond on Morphology and Handedness of Nanostructures

et al. 2013

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Two optically active phthalocyanine derivatives with eight peripheral chiral (S)-4'-(2-methylbutoxy)biphenyl moieties on the β-position of the phthalocyanine ring are synthesized. The circular dichroism (CD) spectra show signals in the Q absorption region for both compounds 1 and 2 in chloroform solution, indicating the effective chiral-information transfer from the peripheral chiral (S)-4'-(2-methylbutoxy)biphenyl side chains to the phthalocyanine chromophore at the molecular level. Their self-assembling properties are further investigated by using electronic absorption and Fourier transform infrared spectroscopy, transmission electronic microscopy, scanning electronic microscopy, X-ray diffraction, and X-ray photoelectron spectroscopy. Experimental results reveal the effect of the metal-coordination bond on molecular packing models in these nanostructures, which in turn results in the self-assembled nanostructures with different morphologies, from nanosheets for 1 to helical nanofibers for 2. In addition, good semiconducting properties of the nanostructures fabricated from phthalocyanine derivatives 1 and 2 are revealed by current-voltage measurements.

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“…( R )-2-Methyl-1-butanol ( 1b ) was prepared using ( S )-methyl 3-hydroxy-2-methylpropionate ( 1b-1 ) (Tokyo Chemical Industry) as a starting material in five steps according to the literature (Scheme a) . ( R )-2-Methyl-1-butanol, 1b : 66% yield, bp 85 °C/196 mmHg, [α] D = +8.00 ( c 1.00, CHCl 3 ).…”

Section: Experimental Sectionmentioning

confidence: 99%

Strictly Alternating Sequences When Copolymerizing Racemic and Chiral Acetylene Monomers with an Organo-Rhodium Catalyst

Yoshida¹,

Mawatari²,

Sasaki³

et al. 2017

Macromolecules

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A racemic mixture and two chiral monomers of 2-methyl-1-butyl propiolate, i.e., rac1, R1, and S1, were stereoregularly polymerized with a catalyst, [Rh(norbornadiene)Cl] 2 , in methanol at 40 °C to obtain the corresponding helical racemic and two chiral polymers, Prac1, PR1, and PS1, and a copolymer, Pco. The 1 H and 13 C NMR spectra of the racemic and chiral polymers differed, although the NMR spectra of their monomers were the same. The structures of the Pco copolymers with different chiral monomer ratios were analyzed using 1D and 2D NMR, optical rotation, circular dichroism (CD), UV−vis, and computational methods to elucidate the stereochemical effect of the chiral monomers together with the polymerization mechanism. The temperature dependence of 1 H and 13 C NMR spectra in line shape and intensity indicated that the helical main chain undergoes restricted rotation around the ester methylene bonds −O−CH 2 − through a three-site jump exchange called an accordion-like helix oscillation (HELIOS). The energetically preferred structures of the helical-sense polymers PR1 or PS1 were simulated using the MMFF94 program. The dependence of the NMR spectral line shapes, optical rotations, and calculated structures on the monomer feed clearly indicated that the copolymers alternatively incorporate R1 and S1 to generate onehanded helical-sense chains. Based on these results, a polymerization mechanism is proposed, explaining a strictly alternating copolymerization that yields helical chains.

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Regio- and Stereochemical Study of Sex Pheromone of Pine Sawfly; Diprion nipponica

Cited by 23 publications

References 19 publications

Volatile Lactones — (5S,S)‐5‐Methyl‐3‐(methylalkyl)furan‐2(5H)‐ones — Identified in the Submerged Cultivation of Streptomyces Avermitilis

Volatile Lactones — (5S,S)‐5‐Methyl‐3‐(methylalkyl)furan‐2(5H)‐ones — Identified in the Submerged Cultivation of Streptomyces Avermitilis

Helical Self‐Assembly of Optically Active Phthalocyanine Derivatives: Effect of ZnO Coordination Bond on Morphology and Handedness of Nanostructures

Strictly Alternating Sequences When Copolymerizing Racemic and Chiral Acetylene Monomers with an Organo-Rhodium Catalyst

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