Efficient and Stereo-Selective Syntheses of Three Stereoisomers of the Sex Pheromone of the Cowpea Weevil,<i>Callosobruchus maculatus</i>

Yajima, Arata; Yamamoto, Masamichi; Nukada, Tomoo; Yabuta, Goro

doi:10.1271/bbb.70309

Cited by 6 publications

(3 citation statements)

References 17 publications

(19 reference statements)

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“…At the same time, however, by NMR spectroscopy the aldehyde was found to be stable under the conditions of the Dess–Martin oxidation for at least one hour, thus suggesting that its further oxidation without isolation might lead to cleaner and higher yielding conversion into the carboxylic acid. This approach could be successfully implemented, such that the addition of NaClO 2 , NaH 2 PO 4 ⋅H 2 O, t BuOH, H 2 O, and 2‐methyl‐2‐butene to the Dess–Martin oxidation mixture furnished the desired carboxylic acid 18 in an excellent yield of 81 % 27. Cleavage of the two secondary TBS ethers in 18 with 5 % aqueous HF in CH 3 CN then gave ripostatin B ( 1 ) in 88 % yield.…”

Section: Methodsmentioning

confidence: 99%

Total Synthesis of the Bacterial RNA Polymerase Inhibitor Ripostatin B

Glaus

Altmann

2012

Angewandte Chemie

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Eine modulare und hoch stereoselektive Synthese der Titelverbindung wurde entwickelt. Schlüsselschritte beim Aufbau des Kohlenstoffgerüsts von Ripostatin B (1; siehe Schema) sind eine stereoselektive Paterson‐Aldolreaktion und eine Ringschlussmetathese in hohen Ausbeuten mit dem Grubbs‐Katalysator der ersten Generation. Die Hydroxygruppe an C15 wurde durch eine Tishchenko‐Evans‐Reduktion mit exzellenter Ausbeute und Selektivität eingeführt.

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Section: Methodsmentioning

confidence: 99%

Total Synthesis of the Bacterial RNA Polymerase Inhibitor Ripostatin B

Glaus

Altmann

2012

Angewandte Chemie

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“…The t-butyldimethylsilyl (TBS) group of 7 was removed under mild conditions to prevent the epimerization of the chiral center (Yajima et al, 2008) to give 8. Finally, the hydroxyl group of 8 was oxidized under mild conditions (Yajima et al, 2007b), and the chiral auxiliary group was carefully removed by LiOH to give the desired (S)-2. The enantiomeric purity of synthetic (S)-2 was determined according to the reported procedure (Yajima et al, 2007a).…”

Section: Synthesis Of Callosobruchusic Acidmentioning

confidence: 99%

Contact Sex Pheromone Components of the Seed Beetle, Callosobruchus analis (F.)

et al. 2010

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Callosobruchus analis (Coleoptera: Chrysomelidae: Bruchinae), found throughout tropical Asia and Africa, is a pest of stored legumes. Previous work has shown that females of this species produce a contact sex pheromone that elicits copulatory behavior in males. Comparisons of copulatory activity between any two of four congeneric species suggest that the contact sex pheromones are species specific. In laboratory bioassays, male C. analis exhibited copulatory behavior to a female dummy to which a crude extract of virgin females was applied. The extract had been collected by a filter paper method and was purified by acid-base partition and chromatographic techniques. Gas chromatography-mass spectrometry (GC-MS) analyses of active fractions revealed that the active compounds were 2,6-dimethyloctane-1,8-dioic acid (1) and callosobruchusic acid, (E)-3,7-dimethyl-2-octene-1,8-dioic acid (2), previously identified as contact sex pheromones of Callosobruchus maculatus (F.) and C. chinensis (L.), respectively. The stereoisomeric and chemical compositions were determined by the 2D-HPLC-Ohrui-Akasaka method as (2S,6R)-1:(S)-2=1.8:1, which meant that both compounds in C. analis were stereochemically pure, unlike the case of C. maculatus and C. chinensis. An examination of the influence of synthetic pheromone compounds on male copulatory activity revealed that (2S,6R)-1 is the main component, and that (S)-2 has an additive effect. In the examination of the stereochemistry-activity relationship, no copulatory behavior was elicited by (2R,6S)-1, and, furthermore, the enantiomer significantly masked the pheromonal activity of (2S,6R)-1. Glass rod dummy assays also suggested the presence of synergists. These results could elucidate the specificity of mate recognition in C. analis.

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“…The three latter compounds have been synthesized by Yajima et al [146]. 57 was prepared using Chong's procedure of alkylation of the dianion of 3-methyl-3-buten-1-ol, followed by sequential Dess-Martin and Pinnick oxidations to give the target molecule in a moderate yield but without isomerization of the somewhat sensitive 3-exo methylene double bond.…”

Section: (E)-and (Z)-3-methyl-4-heptenoic Acid (56) and 3methylenehementioning

confidence: 99%